I2-Mediated [3 + 2] annulation of methyl-azaarenes with alkyl 2-isocyanoacetates or amino acid ester hydrochlorides: selective synthesis of iodine-functionalized and non-iodine-functionalized fused imidazoles

An I2-mediated [3 + 2] annulation of methyl-azaarenes with alkyl 2-isocyanoacetates or amino acid ester hydrochlorides has been demonstrated. This strategy involves C≡N bond cleavage of isocyanides and can selectively synthesize iodine-functionalized and non-iodine-functionalized fused imidazoles. S...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2022-03, Vol.9 (5), p.1403-1409
Main Authors: Yong-Ji, Hu, Zhou, Yu, Jing-Jing, Gao, Zhang, Han, Kai-Rui Yang, Jia-Jun, Li, Xiao-Xin, Yan, Yuan-Lin, Li, Yan-Ping, Zhu
Format: Article
Language:English
Subjects:
Amino acids
Chemical reactions
Hydrochlorides
Imidazole
Iodine
Organic chemistry
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Summary:An I2-mediated [3 + 2] annulation of methyl-azaarenes with alkyl 2-isocyanoacetates or amino acid ester hydrochlorides has been demonstrated. This strategy involves C≡N bond cleavage of isocyanides and can selectively synthesize iodine-functionalized and non-iodine-functionalized fused imidazoles. Scale-up experiments and arylation, alkynylation, alkenylation and selenization of iodine-functionalized products demonstrated the potential applications of this reaction.
ISSN:2052-4110
2052-4110
DOI:10.1039/d1qo01940f