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2001 isoquinoline derivatives isoquinoline derivatives R 0420 13 - 140 Synthesis of Isoquinoline Derivatives by Diels–Alder Reactions of 2(1H)-Pyridones Having and Electron-Withdrawing Group with Methoxy-1,3-butadienes. — Diels–Alder reaction of the N-methyl 2-pyridones (Ia-d) bearing an electron-withdrawing group at C-4 position with methoxybutadienes affords cis-tetrahydoisoquinolone derivatives (III) in complete regio- and stereoselectivity. Aromatization of thus obtained adduct (IIIa) provides an alternative route to the isoquinoline alkaloid (V). Similar cycloaddition reactions of N-unsubstituted pyridones proceed regio- but not stereoselective to give mixtures of cis/trans adducts. — (FUJITA, REIKO; HOSHINO, MASATO; TOMISAWA, HIROSHI; HONGO, HIROSHI; Chem. Pharm. Bull. 48 (2000) 11, 1814-1817; Tohoku Pharm. Univ., Aoba, Sendai 981, Japan; EN) 1

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Page 1: ChemInform Abstract: Synthesis of Isoquinoline Derivatives by Diels—Alder Reactions of 2(1H)-Pyridones Having and Electron-Withdrawing Group with Methoxy-1,3-butadienes

2001 isoquinoline derivatives

isoquinoline derivativesR 0420

13 - 140Synthesis of Isoquinoline Derivatives by Diels–Alder Reactions of2(1H)-Pyridones Having and Electron-Withdrawing Group withMethoxy-1,3-butadienes. — Diels–Alder reaction of the N-methyl2-pyridones (Ia-d) bearing an electron-withdrawing group at C-4 positionwith methoxybutadienes affords cis-tetrahydoisoquinolone derivatives (III) incomplete regio- and stereoselectivity. Aromatization of thus obtained adduct(IIIa) provides an alternative route to the isoquinoline alkaloid (V). Similarcycloaddition reactions of N-unsubstituted pyridones proceed regio- but notstereoselective to give mixtures of cis/trans adducts. — (FUJITA, REIKO;HOSHINO, MASATO; TOMISAWA, HIROSHI; HONGO, HIROSHI; Chem.Pharm. Bull. 48 (2000) 11, 1814-1817; Tohoku Pharm. Univ., Aoba, Sendai981, Japan; EN)

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