Multicomponent reaction of imidazo[1,5-a]pyridine carbenes with aldehydes and dimethyl acetylenedicarboxylate or allenoates: a straightforward approach to fully substituted furans.
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.
Pan
Huan-Rui
HR
College of Chemistry, Beijing Normal University, Beijing 100875, China.
Li
Yong-Jia
YJ
Yan
Cai-Xia
CX
Xing
Juan
J
Cheng
Ying
Y
D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D000480:Alkynes; D005663:Furans; D009281:Naphthalenes; D011725:Pyridines; C554655:imidazo(1,5-a)pyridine; C030011:carbene; C022918:acetylenedicarboxylic acid dimethyl ester; C110055:allenolic acid; D008697:Methane