Journal of Organic Chemistry p. 12552 - 12561 (2015)
Update date:2022-08-17
Topics:
Basceken, Sinan
Kaya, Serdal
Balci, Metin
Gold-catalyzed and NaH-supported intramolecular cyclization of N-propargyl indole derivatives with pyrazole and pyrrole units attached to indole is described. An efficient route to the synthesis of pyrazolodiazepinoindole, pyrazolopyrazinoindole, and pyrrolopyrazinoindole has been established. First, N-propargyl 2-(1H-pyrazol-5-yl)-1H-indole and 2-(1H-pyrrol-2-yl)-1H-indole were synthesized. Introduction of various substituents into the alkyne functionality was accomplished by Sonogashira cross-coupling reaction. Gold-catalyzed cyclization of pyrazoles having a terminal alkyne afforded the 6-exo-dig cyclization product. However, exclusive formation of 7-endo-dig cyclization products was observed with internal alkynes. On the other hand, cyclization with NaH only resulted in the formation of 6-exo-dig cyclization products regardless of the substitution of the alkyne functionality. Allenic intermediates were postulated for this outcome.
View MoreChengdu King-tiger Pharm-chem. Tech. Co., Ltd
Contact:028-85317716
Address:Tianfu Life Science Park, No. 88 South Keyuan Road, Gaoxin District, Chengdu City, Sichuan Province, PRC.
Taizhou Crene Biotechnology co.ltd
Contact:86-576-88813233 88205808
Address:Economic Developed Zone of Taizhou Zhejiang China
Shenzhen Feiming Science and Technology Co,. Ltd
Contact:+86-755-85232577
Address:#B2309, Fenglin International Center ,Jixiang Road, Longcheng street, LongGang District, Shenzhen city, Guangdong province, China.
Contact:0512-63006287
Address:no.88.YISHENG Road,etdz-WUJIANG,SUZHOU,CHINA
shanghai jinshan pharmaceutical Co.,Ltd
Contact:021-57363011,13681638167
Address:No. 7966 Tingfeng Road,Jinshan,Shanghai,China
Doi:10.1080/15421400903483973
(2010)Doi:10.1002/chem.201600158
(2016)Doi:10.1021/acs.orglett.0c00089
(2020)Doi:10.1021/ja01539a039
(1958)Doi:10.1016/j.ejmech.2014.09.053
(2014)Doi:10.1039/b406878e
(2004)