TY - JOUR
T1 - Base-promoted transannulation of heterocyclic enamines and 2,3-epoxypropan-1-ones
T2 - Regio- and stereoselective synthesis of fused pyridines and pyrroles
AU - Yang, Zheng
AU - Hao, Wen Juan
AU - Xu, Hai Wei
AU - Wang, Shu Liang
AU - Jiang, Bo
AU - Li, Guigen
AU - Tu, Shu Jiang
N1 - Publisher Copyright:
© 2015 American Chemical Society.
PY - 2015/3/6
Y1 - 2015/3/6
N2 - Base-promoted transannulation of heterocyclic enamines and 2,3-epoxypropan-1-ones has been successfully achieved, providing a new access to structurally diverse fused pyridines and pyrroles with excellent regio- and stereoselectivity. Treatment with N-aryl 4-aminofuran-2(5H)-ones and 2,3-epoxypropan-1-ones under microwave heating resulted in functional furo[3,2-b]pyridines in good yields. The N-aryl 4-aminopyrrol-2(5H)-ones bearing an electron-withdrawing group engaged in the reaction afforded pyrrolo[3,2-b]pyridines, whereas their counterparts with an electron-neutral or an electron-donating group underwent a different reaction pathway to form pyrrolo[3,2-b]pyrroles through C-C bond cleavage.
AB - Base-promoted transannulation of heterocyclic enamines and 2,3-epoxypropan-1-ones has been successfully achieved, providing a new access to structurally diverse fused pyridines and pyrroles with excellent regio- and stereoselectivity. Treatment with N-aryl 4-aminofuran-2(5H)-ones and 2,3-epoxypropan-1-ones under microwave heating resulted in functional furo[3,2-b]pyridines in good yields. The N-aryl 4-aminopyrrol-2(5H)-ones bearing an electron-withdrawing group engaged in the reaction afforded pyrrolo[3,2-b]pyridines, whereas their counterparts with an electron-neutral or an electron-donating group underwent a different reaction pathway to form pyrrolo[3,2-b]pyrroles through C-C bond cleavage.
UR - http://www.scopus.com/inward/record.url?scp=84924311324&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.5b00067
DO - 10.1021/acs.joc.5b00067
M3 - Article
C2 - 25692388
AN - SCOPUS:84924311324
SN - 0022-3263
VL - 80
SP - 2781
EP - 2789
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 5
ER -