Efficient regioselective five-component synthesis of novel thiazolo[3,2-a]pyridine carbohydrazides and oxazolo[3,2-a]pyridine carbohydrazides.
Cyanoacetohydrazide
Nitroketene acetal
One-pot reaction
Oxazolopyridine
Thiazolopyridine
Journal
Molecular diversity
ISSN: 1573-501X
Titre abrégé: Mol Divers
Pays: Netherlands
ID NLM: 9516534
Informations de publication
Date de publication:
Apr 2023
Apr 2023
Historique:
received:
12
03
2022
accepted:
18
04
2022
medline:
10
5
2023
pubmed:
20
5
2022
entrez:
19
5
2022
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 35587848
doi: 10.1007/s11030-022-10446-0
pii: 10.1007/s11030-022-10446-0
doi:
Substances chimiques
pyridine
NH9L3PP67S
carbohydrazide
W8V7FYY4WH
Acetals
0
Pyridines
0
Ethanol
3K9958V90M
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
667-678Informations de copyright
© 2022. The Author(s), under exclusive licence to Springer Nature Switzerland AG.
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