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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
Author(s) -
Chudík Milostav,
Marchalín Štefan,
Knesl Peter,
Daich Adam,
Decroix Bernard
Publication year - 2000
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570370623
Subject(s) - chemistry , aryl , intramolecular force , derivative (finance) , borohydride , medicinal chemistry , dihydropyridine , lactam , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , alkyl , financial economics , economics , calcium
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.