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Facile access to 6-substituted 1,4,5,7-tetrahydropyrrolo[3,4-b]-pyridines via hantzsch type dimethyl 4-aryl-2-formyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylates

✍ Scribed by Milostav Chudík; Štefan Marchalín; Peter Knesl; Adam Daich; Bernard Decroix

Publisher
Journal of Heterocyclic Chemistry
Year
2000
Tongue
English
Weight
438 KB
Volume
37
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Efficient assembly of 6‐substituted 4‐aryl‐5‐oxo‐1,4,5,7‐tetrahydropyrrolo[3,4‐b]pyridines (7a‐f) is described according to a Hantzsch type reaction from formyl‐ester 4 by imination, borohydride reduction and intramolecular thermal amino‐ester cyclization. The starting compound 4 was prepared in three steps from the readily available formyl derivative 1, methyl 4,4‐dimethoxy‐3‐oxobutanoate and methyl 3‐aminocrotonate.

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