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Ionic‐liquid‐promoted Four‐component One‐pot Synthesis of Highly Functionalized Benzimidazo[2,1‐ b ][1,3]thiazines: Facile Construction of N‐ fused Heterocycles
Author(s) -
Siddiqui I. R.,
Srivastava Anjali,
Shamim Shayna,
Srivastava Arjita,
Waseem Malik A.,
Abumhdi Afaf A. H.,
Srivastava Anushree,
Rai Pragati,
Singh R. K. P.
Publication year - 2013
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300049
Subject(s) - chemistry , ionic liquid , isocyanide , nucleophile , electrophile , carbon disulfide , alkyne , yield (engineering) , ionic bonding , medicinal chemistry , combinatorial chemistry , organic chemistry , ion , catalysis , materials science , metallurgy
A one‐pot, four‐component, efficient, and facile synthesis of highly functionalized benzimidazo[2,1‐ b ][1,3]thiazines promoted by ionic liquid ([bmim]Br)/Et 3 N has been developed. The protocol involves nucleophilic addition of o ‐phenylenediamine to carbon disulfide to give 2‐mercaptobenzimidazole. After nucleophilic addition to the activated olefinic bond of a zwitterionic intermediate, which is generated by reaction of isocyanide with an electrophilic alkyne, subsequent cyclization gives benzimidazo[2,1‐ b ][1,3]thiazines with high atom economy. The ionic liquid was recovered and reused without any appreciable decrease in activity and product yield.