Multicomponent Reaction of Imidazo[1,5-a]pyridine Carbenes with Aldehydes and Dimethyl Acetylenedicarboxylate or Allenoates: A Straightforward Approach to Fully Substituted Furans

• Published in: Journal of organic chemistry 2010-10, Vol.75 (19), p.6644-6652
• Main Authors: Pan, Huan-Rui, Li, Yong-Jia, Yan, Cai-Xia, Xing, Juan, Cheng, Ying
• Format: Article
• Language: English
• Subjects: Aldehydes - chemistry; Alkynes - chemistry; Chemistry; Exact sciences and technology; Free radicals chemistry; Furans - chemical synthesis; Furans - chemistry; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Methane - analogs & derivatives; Methane - chemistry; Molecular Structure; Naphthalenes - chemistry; Organic chemistry; Preparations and properties; Pyridines - chemistry; Reactivity and mechanisms; Stereoisomerism
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo1014933

The facile three-component reactions of N,N-substituted imidazo[1,5-a]pyridine carbenes, namely imidazo[1,5-a]pyridin-3-ylidenes, with aldehydes and DMAD or allenoates were disclosed. Both reactions proceeded via tandem nucleophilic addition, [3 + 2]-cycloaddition, and ring transformation to produce different 4-[(2-pyridyl)methyl]aminofuran derivatives generally in moderate yields. This work not only provided the first example of the application of imidazo[1,5-a]pyridin-3-ylidenes in organic synthesis but also developed a straightforward approach to fully substituted furans that are not easily accessible by other methods.