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Chapter-1
HNGU PATAN 1
INTRODUCTION
CHAPTER-1
Chapter-1
HNGU PATAN 2
CHAPTER-1
INTRODUCTION
1.1 Review on Triazine derivatives
The triazine structure is a heterocyclic ring, analogous to the six-membered
benzene ring but with three carbons replaced by nitrogens. The three isomers of
triazine are distinguished from each other by the positions of their nitrogen atoms, and
are referred to as 1,2,3-triazine, 1,2,4-triazine, and 1,3,5-triazine. Other aromatic
nitrogen heterocycles are pyridines with 1 ring nitrogen atom, diazines with 2
nitrogen atoms in the ring and tetrazines with 4 ring nitrogen atoms. Triazines are
weaker bases than pyridine.
The best known 1,3,5-triazine derivative is melamine with three amino
substituents used in the manufacture of resins. Another triazine extensively used in
resins is benzoguanamine. Triazine compounds are often used as the basis for various
herbicides such as cyanuric chloride (2,4,6-trichloro-1,3,5-triazine). Chlorine-
substituted triazines are also used as reactive dyes. These compounds react through a
chlorine group with hydroxyl groups present in cellulose fibres in nucleophilic
substitution, the other triazine positions contain chromophores. Mixtures of Triazines
and water are also used to remove H2S from natural gas.
A series of 1,2,4-triazine derivatives known as BTPs have been considered in
the liquid-liquid extraction community as possible extractants for use in the advanced
nuclear reprocessing of used fuel. BTPs are molecules containing a pyridine ring
bonded to two 1,2,4-triazin-3-yl groups. Triazine-based molecules have been used as
bridging ligands to bind three dinuclear arene ruthenium (or osmium) compounds to
Chapter-1
HNGU PATAN 3
form metallaprisms. S-Triazine derivatives represent an important class of compounds
due to their potential to be biologically active. They are known to be anti-protozoals, [1], anticancer agents, estrogen receptor modulators, antimalarials, cyclindependent
kinase modulators, [2] and antimicrobials. Cyanuric chloride, an inexpensive, easily
available reagent, of low toxicity and less corrosive than other similar reactants, has
been widely used in organic reactions. 1,3,5-triazines (or s-triazines) are a class of
compounds well known for a long time and still continue the object of considerable
interest mainly due to their application in different fields, including the production of
herbicides and polymer photostabilizers. Some 1,3,5-triazines display important
biological properties; for example hexamethylmelamine (HMM) & 2-amino-4-
morpholino-s-triazine are used clinically due to their antitumor properties to treat
lung, breast and ovarian cancer, respectively. [3]
The diverse biological activities
observed for different molecule containing the 1,3,5-triazine unit have been further
explored in order to discover other new potential molecules through the synthesis of
libraries by combinatorial approaches. Certain 1,3,5-triazine derivatives are also used
as chiral stationary phases, for example, the chiral solvating agent for the
determination of enantiomeric excess by NMR spectroscopy and determination of
absolute configuration by circular dichroism.
Thus owing to the above stated importance of this ligand having s-triazine and
8 -hydroxyquinoline (8-HQ) and their systematic literature survey we were interested
to synthesize coordination polymers based on ligands prepared from s-triazine-ether,
5-amino 8-Hydroxyquinoline and various phenol.
I.B.Johns and H. R. Dipietro [4] reported structure of trimer of salicylonitrile,
2,4,6-tris(2-hydroxy phenyl)-s-triazine suggest that it should be coordinate with
divalent tetracoordinate metal ion to form polymeric products.
Chapter-1
HNGU PATAN 4
N
N
N
R
OH OH N
N
N
R
O O
O
M M
R =
Patrick Gamez, Paul de Hoog and Olivier Roubeau [5]
work on Copper(II)
nitrate reacts with the rigid polydentate triple-connecting 2,4,6-(di-pyridin-2-yl-
amino)-[1,3,5]triazine (dpyatriz) ligand in acetonitrile to an unprecedented infinite
molecular ladder in which five-coordinated copper pseudo-dimers are bridged by
nitrate anions and the coordination polymer chains are linked by hexacoordinated
copper ions leading to the formation of large guest cavities
Megumu Munakata and Ming Wen and Yusaku Suenaga [6] work on carbon
and nitrogen coordinated silver (I) polymers of 2,4,6-triphenoxy-1,3,5-triazine. For
the purpose of furthering the understanding of steric structure effects upon
coordination behavior and exploring the possibility of non-planar complexation in the
triazine system for formation of extended polymeric structures, 2,4,6-triphenoxy-
1,3,5-triazine(tpotz) has been reacted with silver(I) perchlorate and
trifluoromethanesulfonate. The crystal structures of [Ag2(tpotz)3(ClO4)2] and
Chapter-1
HNGU PATAN 5
[Ag2(tpotz)2(CF3SO3)2(THF)] have been determined by single-crystal X-ray
diffraction. Tpotz is rich in organic components that can offer potential sites for
complexation, which can be utilized to generate an interesting array of organometallic
compounds with one-dimensional chains.
Patrick Gamez, Paul de Hoog and Martin Lutz[7]
studied on coordination
compounds from 1,3,5-triazine derived multi-directional ligands which useful for
oxidation catalysis. A series of 1,3,5-triazine- and 2,2-dipyridylamine-based ligands
have been prepared and the crystal structure from one of them was solved. The
coordination of these dendritic multi-directional ligands with various metal salts led to
attractive supramolecular architectures.
N
N
N
O
OO
tpotz
CF3SO3
Ag(1)
Ag(1)
CF3SO3
Schematic view of anion coordinated chain
Chapter-1
HNGU PATAN 6
N
N
N
Cl
ClCl
N
N
N
N
ClCl
R1 R1
N
N
N
N
ClCl
R1 R1
N
N
N
N
NCl
R1 R1
R2
R2
N
N
N
N
NCl
R1 R1
R2
R2
N
N
N
N
NN
R1R1
R2
R2
R3
R3
R12NH
R22NH
R32NH
Oo C
25o C
67o C
THF; DIPEA; Ar; 2 hrs
THF; DIPEA; Ar; 12 hrs
THF; DIPEA; Ar; 24 hrs
Differential reactivity of 1,3,5-triazines
N
N
N N
N
N
N
N
N
N
NNN
N
NN
NN
N O
N
N
NH
N
N
N
N
N
N
N
O
N N
NH
N N
N
NN
NN
N N
N NH
O N
N
Ligands prepared and tested in catechol oxidase activity
Chapter-1
HNGU PATAN 7
Yongquin wei, kechen wu and Ria broer [8] work on a polymeric cobalt
compound [Co(DCNT)(H2O)]n with novel topology: Synthesis, structure,
luminescence, and magnetic property. The hydrothermal reaction of Co(NO3)2. 6H2O
and a new designed ligand H2DCNT yields a three-dimensional polymer [Co(DCNT)
(H2O)]n (1), H2DCNT=2,4-bis(4-carboxyphenylamino)-6-diethylamino-1,3,5-
triazine. In the structure [Co(DCNT) (H2O)]n each DCNT2- has three coordination
sites, one nitrogen atom in the triazine ring coordinating to Co(II) and two
carboxylates adopting bridging mode, which make the infinite Co(II) chains array
uniformly and evenly toward crystallographic c-axis. Luminescent and magnetic
properties of [Co(DCNT) (H2O)]n
were also studied.
N
N
N
Cl
ClCl
N
N
N
ClClN N
N NH
NH
N
C2H5
H5C2
COOH
COOH
+ 2 NH(C2H5)2Acetone
00C
N(C2H5)2
4-Amino benzoic acid
450C
The structure and synthetic route of H2
DCNT
Vinod kumar pandey, Sarah Tusi and Zehra Tusi [9]
reported synthesis and
biological activity of substituted 2,4,6-s-triazine derivatives.
N N
N
O
OH
R' R
O
OH
R'
R
O
OH
R
R'
Chapter-1
HNGU PATAN 8
Jignesh P. Raval, Amrita R. Rai and Nilesh H. Patel [10] reported synthesis and
invivo antimicrobial activity of N’-[4(arylamino)-6-(pyridin-2-ylamino)1,3,5-triazin-
2-yl]benzohydrazide. Here, variety of N'-(4-(arylamino)-6-(pyrazin-2-ylamino)-1,3,5-
triazin-2-yl)isonicotinohydrazide, were synthesized by using 2-aminopyridine,
isonicotinic acid hydrazide and cyanuric chloride. And the structures of these
compounds were confirmed by IR, NMR (1H & 13
C) spectral analysis. The newly
synthesized compounds were also evaluated for antimicrobial activity against variety
of bacterial strains and some of these compounds have shown significant antibacterial
and antifungal activities.
N
NN
NNH
NH
NH
NH
O
R
Sonika jain, Anamika Sharma, Meenakshi Agrawal [11]
reported synthesis and
antimicrobial evaluation of some novel trisubstituted s-triazine derivatives based on
isatinimino, sulphonamido and Azacarbazole.
N
NH
N O
R
N NH
N
N
N
NH
S NH
O
O
R'
O
Chapter-1
HNGU PATAN 9
K. N. Sarmah, N. K. Sarmah and Talha V. Patel [12]
studied synthesis,
characterization and antimicrobial studies of certain triazole containing s-triazine
derived compounds.
N
NNNH
N
N
N
NH S
NH
OMe
NH
OR
G. R. Jani, K. B. Vyas and Zudas Franco [13]
reported preparation and
antimicrobial activity of s-triazine hydrazones of 7-hydroxy coumarin.
OO OH
NCH3 NH
N
N
N
Cl
Cl
K. N. Sarmah, N. K. Sarmah and K. B. Kurmi [14]
reported synthesis of novel
s-triazine derivatives as potential antibacterial agents.
N
N
N
R1
R3R2
Chapter-1
HNGU PATAN 10
Compounds R1 R2 R3
1a Dicyclohexylamine N-methyl piperazine -Cl
1b Dicyclohexylamine Monoethanolamine -Cl
2a Benzimidazole 2-chlorophenylthiourea 2-chloro aniline
2b Benzimidazole 4-chlorophenylthiourea 4-chloroaniline
2c Benzimidazole 4-chlorophenylthiourea 4-fluoroaniline
2d Benzimidazole 3-methylphenylthiourea 3-methyl aniline
K. N. Sarmah, N. K. Sarmah and K. B. Kurmi [15]
reported synthesis and
studies of antifungal activity of 2,4,6-tri substituted 1,3,5-triazines
N
N
N
R1
R3R2
Compounds R1 R2 R3
1a Benztriazole Cyclo hexyl amine Thiourea of m-Toluidine
1b Benztriazole Cyclo hexyl amine Thiourea of O-Toluidine
1c Benztriazole Cyclo hexyl amine Thiourea of p-Toluidine
1d Benztriazole Cyclo hexyl amine Thiourea of p-chloro aniline
1e Benztriazole Cyclo hexyl amine Thiourea of p-anisidine
1f Benztriazole Cyclo hexyl amine Thiourea of p-bromo aniline
2a Benztriazole Benzimidazole Urea of p-chloro aniline
2b Benztriazole Benzimidazole Urea of p-chloro aniline
3a Dicyclo hexyl
amine
Mono ethanol amine -
3b Dicyclo hexyl
amine
N-methyl piperazine -
Chapter-1
HNGU PATAN 11
Firdous D. Khan, Manjusha V. Yadav and Ashok D. Sagar [16]
reported
synthesis, characterization and antimicrobial evaluation of core s-triazine moiety.
N
N
N
O
OO
CHO
CHO
OHC
G. Jagadeesh kumar, H. V. S. sriramkumar bomma, E. srihari and shweta
srivastava [17]
reported synthesis and anticancer activity of some new s-triazine
derivatives.
N
N
N
N
NN
N
N
N
N
NN
N
NCHF2
N
N
N
NNOO
S
N
N
N
N
NH
OHN
N
N
N
NH
NH
NH
MeO
OMe
OMe
Chapter-1
HNGU PATAN 12
Viktor Milata, Ladislav Reinprecht and Juraj Kizlink [18]
reported synthesis
and antifungal efficacy of 1,3,5-triazines.
N NN
NNN
NN
N
N
N
N
N
N
NN
N
N
N
N
N
NN
N N
NN
N
N
N
CH3
CH3
CH3
CH3CH3
CH3N
N
NN
N
N
N
N
N
Ph
Ph
PhPh
Ph
Ph
Anjani solankee, Kishor kapadia, Ana ciric, Marina sokovic and irini
doytchinove [19]
reported synthesis of some new s-triazine based chalcones and their
derivatives as potent antimicrobial drugs.
Chapter-1
HNGU PATAN 13
NN
N
N
N
NH
NH
NH
R
COCH3 N NH2
RCN
N
N
N
NH
NH
NH
N N
R
NH2
N
N
N
NH
NH
NH
Pankaj B. Kaswala, Kishor H. Chikhaliya [20]
design, synthesis and
antimicrobial evaluation of s-triazinyl urea and thio urea derivatives.
O
O
N
N
N
NH
NHO
NH X
R
Carlos A. M. Afonso and co-workers [21]
reported synthesis of 2,4,6-tri-
substituted -1,3,5-triazines.
Nidhi Gautam and O P Chaourasia [22]
isooxazoline and isothiazoline moiety
reported synthesis, characterization and
insecticidal activity of some new s-triazine derivatives of pyrazoline, pyrimidine,
Chapter-1
HNGU PATAN 14
N
N
N
NH
OMe
NH
MeO
NH
CH
OCH
R
Ramachndra S. Hosmane, Mitchell A. Rossman [23]
reported synthesis and
structure of s-triazine.
Loredana Donati and Enzo Funari [24]
reported review on leaching
characteristics of triazines and their degradation products.
Kokila N. Sarmah and Talha V. Patel [25]
reported synthesis, characteristics
and antimicrobial studies of certain s-triazine derived compounds and analogs.
N
N
N
NH
NH
NO
X
NH
NNO
SCH3
R
Chapter-1
HNGU PATAN 15
Edwin M. Smolin and Lorence Rapoport [26]
published book series on s-
triazine and its derivatives. Both author basically from Central research division,
Americal Cyanamid company, Stanford, Connecticut, USA.
Akshay D. Desai, Dharmesh H. Mahajan and Kishor H. Chikhalia [27]
reported
synthesis of novel aliphatic thiourea derivatives containing s-triazine moiety as
potential antimicrobial agents.
R
S
N
N
N
NH
NNH
O
NH
O
NH
S
K. N. Sarmah, N. K. Sarmah and K. B. Kurmi [28]
studied synthesis and studies
of biological evaluation of certain s-triazine derived compounds.
NN
N
N
N
N
N
N
NH
NH
O R
Sweta D. Desai and Arvind G. Mehta [29]
reported design, synthesis and
biological evaluation of various N-substituted piperazine annulated s-triazine
derivatives.
Chapter-1
HNGU PATAN 16
OO
N
N
N
N
O
N
R
OMe
S. G. Kansara, R. D. Pandit and V. G. Bhawe [30]
reported synthesis of some
new ibuprofen derivatives containing heterocyclic moiety like s-triazine and evaluated
for their analgesic activity.
NH
O
CH3
CH3
CH3
R
N
N
N
Cl
NH
O
CH3
CH3
CH3
R
Vineeta sareen, vineeta khatri and Prakash jain [31]
reported synthesis of 2-(6-
fluorobenzothiazole-2’-yl amino)-4-(phenylthioureido)-6-(substituted thioureido)-
1,3,5-triazine as antimicrobial agent.
N
S
N
N
N
NHCSNHR
C6H5NHCSNH NH F
Chapter-1
HNGU PATAN 17
N. sekar, Vikas S. padalkar and Kiran R Phatangare [32]
reported synthesis and
biological evaluation of novel 6-aryl-2,4-di substituted Schiff bases 1,3,5-triazine
derivatives as antimicrobial agents.
ONN
NN
O
N
N
ONN
NN
O
N
N Cl
Cl
ONN
NN
O
N
N OMe
OMe
ONN
NN
O
N
N
Vikas S. padalkar and Vikas S. Patil [33]
reported synthesis and photo physical
properties of fluorescent 1,3,5-triazine styryl derivatives. It was found that the strong
electron acceptor-donor chromophoric system of these compounds showed high
Stoke’s shift and excellent thermal stability. Compounds showed positive
solvatofluorism behaviour from nonpolar to polar solvent. All compounds have good
thermal stability.
Chapter-1
HNGU PATAN 18
ON
NN
O
N
CN
CN
CN
CNO
NN
NO
N
CN
CN
COOEt
COOEt
ON
NN
O
N
CN
CN
Ph
Ph ON
NN
O
N
CN
CN
O2N
O2N
SN
SN
ON
NN
O
N
CN
CN
Divya Karunakaram, Govindarajan R. and Srikanth Jupudi [34]
reported
synthesis and biological evaluation of newer s-triazine derivatives.
N
N
N
NH
ClCl
N X
R
Chapter-1
HNGU PATAN 19
1.2 Brief details on Morpholine containing compounds and its
biological activity
Morpholine [35] is an organic chemical compound having the chemical formula
O(CH2CH2)2NH. This heterocycle features both amine and ether functional groups.
Because of the amine, morpholine is a base; its conjugate acid is called
morpholinium. For example, treating morpholine with hydrochloric acid makes the
salt morpholinium chloride.
NH
O Morpholine is a common additive, in parts per million concentrations, for pH
adjustment in both fossil fuel and nuclear power plant steam systems. Morpholine is
used because its volatility is about the same as water, so once it is added to the water,
its concentration becomes distributed rather evenly in both the water and steam
phases. Its pH adjusting qualities then become distributed throughout the steam plant
to provide corrosion protection. Morpholine is often used in conjunction with low
concentrations of hydrazine or ammonia to provide comprehensive all-volatile
treatment chemistry for corrosion protection for the steam systems of such plants.
Morpholine decomposes reasonably slowly in the absence of oxygen at the high
temperatures and pressures in these steam systems.
Morpholine derivatives used as agricultural fungicides in cereals are known as
ergosterol biosynthesis inhibitors
[1] Amorolfine
O
N
Chapter-1
HNGU PATAN 20
Amorolfine (or amorolfin), is a morpholine antifungal drug that inhibits D14
reductase and D7-D8 isomerase [36], which depletes ergosterol and causes ignosterol to
accumulate in the fungal cytoplasmic cell membranes. Marketed as Curanail, Loceryl,
Locetar, and Odenil, amorolfine is commonly available in the form of a nail lacquer,
containing 5% amorolfine as the active ingredient. It is used to treat onychomycosis
(fungal infection of the toe- and fingernails). Amorolfine 5% nail lacquer in once-
weekly or twice-weekly applications has been shown in two studies to be between
60% and 71% effective in treating toenail onychomycosis; complete cure rates three
months after stopping treatment (after six months of treatment) were 38% and 46%.
However, full experimental details of these trials were not available and since they
were first reported in 1992 there have been no subsequent trials. [2] Fenpropimorph
O
N
Fenpropimorph is a morpholine-derived fungicide used in agriculture,
primarily on cereal crops such as wheat. [3] Tridemorph
O
NCH3
Tridemorph is a fungicide used to control Erysiphe graminis. It was developed
by BASF in the 1960s who use the trade name Calixin. The World Health
Organization has categorised it as a Class II "moderately hazardous" pesticide because
it is believed harmful if swallowed and can cause irritation to skin and eyes.
Chapter-1
HNGU PATAN 21
In many commercial drugs also contains Morpholine as a active site which is
medicinally active some of these reported here.
[4] Phenmetrazine
O
NH
Phenmetrazine (Preludin) is a stimulant drug containing a phenethylamine
skeleton, in which the terminal amine is incorporated into a morpholine ring, that was
previously used as an appetite suppressant, but has since been withdrawn from the
market. It was initially replaced by its analogue phendimetrazine which functions as a
prodrug to phenmetrazine, but now it is rarely prescribed, due to concerns of abuse
and addiction.
[4] Levofloxacin
N
OO
OH
FN
N
O
Levofloxacin [37] (trade names Levaquin (US), Tavanic (EU), and others) is a
broad spectrum antibiotic of the fluoroquinolone drug class, and the levo isomer of its
predecessor ofloxacin. Its spectrum of activity includes most strains of bacterial
pathogens responsible for respiratory, urinary tract, gastrointestinal, and abdominal
Chapter-1
HNGU PATAN 22
infections, including Gram negative (Escherichia coli, Haemophilus influenzae,
Klebsiella pneumoniae, Legionella pneumophila, Moraxella catarrhalis, Proteus
mirabilis, and Pseudomonas aeruginosa), Gram positive (methicillin-sensitive but not
methicillin-resistant Staphylococcus aureus, Streptococcus pneumoniae,
Staphylococcus epidermidis, Enterococcus faecalis, and Streptococcus pyogenes), and
atypical bacterial pathogens (Chlamydophila pneumoniae and Mycoplasma
pneumoniae). Compared to earlier antibiotics of the fluoroquinoline class such as
ciprofloxacin, levofloxacin exhibits greater activity toward Gram-(+) bacteria but
lesser activity toward Gram-(−) bacteria, especially Pseudomonas aeruginosa.
Levofloxacin and later generation fluoroquinolones are collectively referred to as
"respiratory quinolones" to distinguish them from earlier fluoroquinolones which
exhibited modest activity toward the important respiratory pathogen Streptococcus
pneumoniae.
1.3 Research gaps about the novel 2,4,6-tri substituted-1,3,5-
triazine derivatives.
The usage of most antimicrobial agents is limited, not only by the rapidly
developing drug resistance, but also by the unsatisfactory status of present treatments
of bacterial and fungal infections and drug side-effects [38]
. Therefore, the
development of new and different antimicrobial drugs is a very important objective
and many research programs are directed the design of new antimicrobial agents.
As per the review about the derivatization of various 1,3,5-triazine derivatives,
It is a six-membered heterocycles containing three nitrogen in the ring and its
derivatives have biological activities such as antibacterial, antifungal,
antimycobacterial, anti-inflammatory, analgesic, anticancer, antihypertensive,
anticonvulsant, antiviral, antidepressant, antiasthmatic, diuretic and hypoglycemic.
All these facts were driving force to develop novel 1,3,5-triazine derivatives with
wide structural variation. Thus 1,3,5-triazine derivatives plays pivotal role in
medicinal chemistry.
Chapter-1
HNGU PATAN 23
Here, we are trying to attached a active compounds like 5-(4-Fluoro-phenyl)-
[1,3,4]oxadiazole-2-thiol, 2-Methyl-quinoline-8-amine, 9-ethyl-9H-carbazol-3-amine,
4,5,6,7-Tetrahydro-thieno[2,3-b] pyridine and 4-Amino-N-pyrimidin-2-yl-benzene
Sulfonamide with 1,3,5-triazine, which is already part of existing commercial
pharmaceuticals. Hence, here we are trying to develop new moiety which having good
or better activity then existing pharmaceuticals.
Moreover these substitutions have been studied extensively because of their
ready accessibility, diverse chemical reactivity and broad spectrum of biological
activity. The area in which such a 2,4,6-tri substituted 1,3,5-triazine derivatives has
not been reported so far. Hence, it was thought to undertaken such study.
1.4 Objectives of the present work:
In view of above review, the prime objectives of the present thesis are,
Preparation of various novel 2,4,6-tri substituted-1,3,5-triazine derivatives.
Evaluation of antimicrobial activity of above prepared heterocycles.
Chapter-1
HNGU PATAN 24
1.5 The present work:
According to the above objectives, research work was carried and distributed
into following chapters of the present thesis.
Chapter-2 of the thesis comprises into two sections.
Section-A comprises the details about techniques used for characterization.
Section-B deals with the details about the raw materials used for synthesis. These are
as follow.
(i) Cyanuric chloride,
(ii) Amino oxadiazole,
(iii) 2-Methyl-quinoline-8-amine
(iv) 9-ethyl-9H-carbazol-3-amine
(v) 4,5,6,7-tetrahydrothieno[3,2-b]pyridine
(vi) Sulfapyrimidine
Chapter-3 of the thesis comprises the synthesis and characterization of 2-(4-
flourophenyl-1,3,4-oxadiazoleyl)-5-thio-4-(morpholino)-6-(arylamino)-s-triazine
derivatives.
Chapter-4 of the thesis comprises the synthesis and characterization of N-(9-
Ethyl-9H-carbazol-3-yl)-6-morpholin-4-yl-N’-aryl amine-[1,3,5]triazine-2,4-diamine
derivatives.
Chapter-5 of the thesis comprises the synthesis and characterization of N-(2-
Methyl-quinolin-8-yl)-6-morpholin-4-yl-N'-aryl amine-[1,3,5]triazine-2,4-diamine
derivatives.
Chapter-1
HNGU PATAN 25
Chapter-6 of the thesis comprises the synthesis and characterization of [4-(5,6-
Dihydro-4H-thieno[2,3-b]pyridin-7-yl)-6-morpholin-4-yl-[1,3,5]triazin-2-yl]-phenyl-
amine derivatives.
Chapter-7 of the thesis comprises the synthesis and characterization of 4-(4-
Morpholin-4-yl-6-phenylamino-[1,3,5]triazin-2-ylamino)-N-pyrimidin-2-yl-
benzenesulfonamide derivatives
All the prepared compounds mentioned in chapters-3 to 7 were screened for
their antimicrobial activity. The common biospecies have been selected. The results
of such study are discussed in chapter-8.
The entire synthetic route is scanned in Scheme 1.1 to 1.5.
Chapter-1
HNGU PATAN 26
N N
N ClCl
Cl N N
N Cl
Cl
O
NN
F
SO
NN
SHF
O
NH
N N
N
Cl
O
NN
F
S N
ONH2
R
N N
NO
NN
F
S N
O
NH
R
+THF / 10% NaHCO3
0-50C
THF / 10% NaHCO3
40-450C
+
Dioxane / 10% NaHCO3
100-1100C
(1)(2) (3)
(4)
(5a-j)
(6a-j)
2,4,6-Trichloro-[1,3,5]triazine 5-(4-Fluoro-phenyl)-[1,3,4]oxadiazole-2-thiol 2,4-Dichloro-6-[5-(4-fluoro-phenyl)
-[1,3,4]oxadiazol-2-ylsulfanyl]-[1,3,5]triazine
Morpholine
2-Chloro-4-[5-(4-fluoro-phenyl)-[1,3,4]oxadiazol-2-ylsulfanyl]-6-morpholin-4-yl-[1,3,5]triazine
2-(4-fluoro phenyl-1,3,4-oxadiazoleyl)-5-thio-4-(morpholino)-6(arylamino)-s-triazine derivatives
Where, R = 4-CH3, 4-F, 3-Cl-4-F, 4-NO2, 4-OCH3, 3-CH3, 4-Br, 4-OCOCH3, 3-Cl, 4-Cl
Scheme 1.1
Chapter-1
HNGU PATAN 27
N N
N ClCl
Cl
O
NH
NH2
R
N
NH2
N
NH
N N
N ClCl
N
O
NNH
N
NN
Cl
NH
NO
N
NH
N N
N
R
+THF / 10% NaHCO3
0-50C
THF / 10% NaHCO3
40-450C
+
Dioxane / 10% NaHCO3
100-1100C
(1)(8)
(5a-j)
(10a-j)
2,4,6-Trichloro-[1,3,5]triazine
Morpholine
(7)9-Ethyl-9H-carbazol-3-ylamine (4,6-Dichloro-[1,3,5]triazin-2-yl)-
(9-ethyl-9H-carbazol-3-yl)-amine
(4-Chloro-6-morpholin-4-yl-[1,3,5]triazin-2-yl)-(9-ethyl-9H-carbazol-3-yl)-amine
(9)
N-(9-Ethyl-9H-carbazol-3-yl)-6-morpholin-4-yl-N'-aryl amine-[1,3,5]triazine-2,4-diamine derivatives
Where, R = H, 2-CH3, 3-CH3, 4-CH3, 2-Cl, 3-Cl, 4-Cl, 2-NO2, 3-NO2, 4-NO2
Scheme 1.2
Chapter-1
HNGU PATAN 28
N N
N ClCl
Cl
O
NH
NH2
R
NNH2
CH3
N N
N Cl
Cl
N
NH
CH3
O
N
N N
N
Cl
N
NH
CH3
NH
O
N
N N
N
N
NH
CH3
R
+THF / 10% NaHCO3
0-50C
THF / 10% NaHCO3
40-450C
+
Dioxane / 10% NaHCO3
100-1100C
(1) (12)
(5a-j)
(14a-j)
2,4,6-Trichloro-[1,3,5]triazine
Morpholine
2-Methyl-quinolin-8-ylamine(11)
(4,6-Dichloro-[1,3,5]triazin-2-yl)-(2-methyl-quinolin-8-yl)-amine
(13)(4-Chloro-6-morpholin-4-yl-[1,3,5]-triazin-2-yl)-(2-methyl-quinolin-8-yl)-amine
N-(2-Methyl-quinolin-8-yl)-6-morpholin-4-yl-N'-aryl amine-[1,3,5]triazine-2,4-diamine derivatives
Where, R = H, 2-CH3, 3-CH3, 4-CH3, 2-Cl, 3-Cl, 4-Cl, 2-NO2, 3-NO2, 4-NO2
Scheme 1.3
Chapter-1
HNGU PATAN 29
N N
N ClCl
Cl
O
NH
NH2
R
NH
S
N
N N
N
O
N
S
N
N N
N Cl
Cl
SNH
S
N
N N
N
Cl
O
N
R
+THF / 10% NaHCO3
0-50C
+
Dioxane / 10% NaHCO3
100-1100C
(1)
(16)
(5a-j)
(18a-j)
2,4,6-Trichloro-[1,3,5]triazine (15)
(17)
4,5,6,7-Tetrahydro-thieno[2,3-b]pyridine
7-(4,6-Dichloro-[1,3,5]triazin-2-yl)-4,5,6,7-tetrahydro-thieno[2,3-b]pyridine
7-(4-Chloro-6-morpholin-4-yl-[1,3,5]triazin-2-yl)-4,5,6,7-tetrahydro-thieno[2,3-b]pyridine
[4-(5,6-Dihydro-4H-thieno[2,3-b]pyridin-7-yl)-6-morpholin-4-yl-[1,3,5]triazin-2-yl]-phenyl-amine derivative
Morpholine
THF / 10% NaHCO3
40-450C
Where, R = H, 2-CH3, 3-CH3, 4-CH3, 2-Cl, 3-Cl, 4-Cl, 2-NO2, 3-NO2, 4-NO2
Scheme 1.4
Chapter-1
HNGU PATAN 30
N N
N ClCl
Cl
O
NH
NH2
R
NH2 S NH
O
O N
N
N N
N NH
Cl
Cl S NH
O
O N
N
N N
N NH
Cl
S NH
O
O N
NO
N
NH
N N
N NH
S NH
O
O N
NO
N
R
+
THF / 10% NaHCO3
40-450C
(1)(20)
(5a-j)
(22a-j)
2,4,6-Trichloro-[1,3,5]triazine
Morpholine
(19)
(21)
4-Amino-N-pyrimidin-2-yl-benzenesulfonamide
4-(4,6-Dichloro-[1,3,5]triazin-2-ylamino)-N-pyrimidin-2-yl-benzenesulfonamide
THF / 10% NaHCO3
0-50C
4-(4-Chloro-6-morpholin-4-yl-[1,3,5]triazin-2-ylamino)-N-pyrimidin-2-yl-benzenesulfonamide
+
Dioxane / 10% NaHCO3
100-1100C
4-(4-Morpholin-4-yl-6-phenylamino-[1,3,5]triazin-2-ylamino)-N-pyrimidin-2-yl-benzenesulfonamidederivatives
Where, R = H, 2-CH3, 3-CH3, 4-CH3, 2-Cl, 3-Cl, 4-Cl, 2-NO2, 3-NO2, 4-NO2
Scheme 1.5
Chapter-1
HNGU PATAN 31
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HNGU PATAN 32
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