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. 2023 Apr;27(2):667-678.
doi: 10.1007/s11030-022-10446-0. Epub 2022 May 19.

Efficient regioselective five-component synthesis of novel thiazolo[3,2-a]pyridine carbohydrazides and oxazolo[3,2-a]pyridine carbohydrazides

Hadiseh Rouzban  1 , Mohammad Bayat  2 , Hajar Hosseini  1
Affiliations

Efficient regioselective five-component synthesis of novel thiazolo[3,2-a]pyridine carbohydrazides and oxazolo[3,2-a]pyridine carbohydrazides

Hadiseh Rouzban et al. Mol Divers. 2023 Apr.

Abstract

Two new categories of fused pyridines include 2H-thiazolo[3,2-a]pyridine-6-carbohydrazides and 2H-oxazolo[3,2-a]pyridine-6-carbohydrazides have been successfully synthesized via five-component cascade reactions using 9-fluorenone, cyanoacetohydrazide, 1,1-bis(methylthio)-2-nitroethene, aromatic aldehydes and cysteamine hydrochloride or ethanol amine as starting materials. This new approach involves a subsequence of key steps: N,S-acetal or N,O-acetal formation, Knoevenagel condensation, Michael addition, tautomerization and N-cyclization. It also has some advantages, such as convenience of operation, tolerance of a wide diversity of functional groups, use of green solvent and ease of purification by washing the crude products with ethanol.

Keywords: Cyanoacetohydrazide; Nitroketene acetal; One-pot reaction; Oxazolopyridine; Thiazolopyridine.

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