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Domino Reaction of Acyclic α,α‐Dialkenoylketene S , S ‐Acetals and Diamines: Efficient Synthesis of Tetracyclic Thieno[2,3‐ b ]thiopyran‐Fused Imidazo[1,2‐ a ]pyridine/Pyrido[1,2‐ a ]pyrimidines
Author(s) -
Liang Fushun,
Zhang Jiqing,
Tan Jing,
Liu Qun
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200606134
Subject(s) - chemistry , thiopyran , ring (chemistry) , imidazole , thiophene , pyridine , domino , medicinal chemistry , catalysis , pyrimidine , aryl , stereochemistry , organic chemistry , alkyl
A series of unusual fused tetraheterocyclic compounds 3 , consisting of a thiopyran (ring A), a thiophene (ring B), a pyridine (ring C), and an imidazole or a pyrimidine (ring D) core, with a bridgehead nitrogen and an angular methyl group, were successfully synthesized by a catalyst‐free, one‐pot, two‐component domino reaction of 4‐(4‐methyl‐1,3‐dithiol‐2‐ylidene)‐1,7‐bis(aryl/heteroaryl)hepta‐1,6‐diene‐3,5‐dione 2 and diamines. In this reaction, up to five new bonds were formed accompanied by the CS bond cleavage of the 1,3‐dithiole ring of 2 , with water as the only by‐product.