TY - JOUR
T1 - A one-pot approach to ethyl 1,4,5-triaryl-1H-pyrazole-3-carboxylates via an improved claisen condensation-knorr reaction sequence
AU - Zhai, Jiaojiao
AU - Gu, Chunhui
AU - Jiang, Jianan
AU - Zhang, Shunli
AU - Liao, Daohua
AU - Wang, Lei
AU - Zhu, Dunru
AU - Ji, Yafei
PY - 2013/12
Y1 - 2013/12
N2 - A one-pot approach to ethyl 1,4,5-triaryl-1H-pyrazole-3-carboxylates has been developed in moderate to high yields. The tert-BuOLi-mediated Claisen condensation of 1,2-diarylethanones and ethyl oxalyl chloride efficiently provided the enolized lithium salts of ethyl 2,4-dioxo-3,4-diarylbutanoates, which in situ reacted with arylhydrazine hydrochlorides via a hydrochloric acid-promoted Knorr reaction to produce the exquisite triarylpyrazole-3- carboxylates. The procedure promises a convenient access to this highly crowded framework for drug discovery.
AB - A one-pot approach to ethyl 1,4,5-triaryl-1H-pyrazole-3-carboxylates has been developed in moderate to high yields. The tert-BuOLi-mediated Claisen condensation of 1,2-diarylethanones and ethyl oxalyl chloride efficiently provided the enolized lithium salts of ethyl 2,4-dioxo-3,4-diarylbutanoates, which in situ reacted with arylhydrazine hydrochlorides via a hydrochloric acid-promoted Knorr reaction to produce the exquisite triarylpyrazole-3- carboxylates. The procedure promises a convenient access to this highly crowded framework for drug discovery.
KW - 2,4-dioxo-3,4-diarylbutanoates
KW - Claisen condensation
KW - Knorr reaction
KW - one-pot approach
KW - triarylpyrazole-3-carboxylates
UR - http://www.scopus.com/inward/record.url?scp=84890791593&partnerID=8YFLogxK
U2 - 10.1002/cjoc.201300776
DO - 10.1002/cjoc.201300776
M3 - 文章
AN - SCOPUS:84890791593
SN - 1001-604X
VL - 31
SP - 1526
EP - 1538
JO - Chinese Journal of Chemistry
JF - Chinese Journal of Chemistry
IS - 12
ER -