
Tetrahedron p. 3745 - 3764 (1998)
Update date:2022-08-03
Topics:
Bast, Klaus
Durst, Toni
Huisgen, Rolf
Lindner, Klaus
Temme, Robert
The cycloadducts of isoquinoline N-phenylimide and ethylenic dipolarophiles are a new class of ene-phenylhydrazines. Their hydrazo rearrangement corresponds to the key step of Fischer's indole synthesis, but the reaction stops at the 2-aminoindoline stage, e.g., 16, because too much strain would build up in the 8-membered ring on indole formation. The model 23, lacking the medium-sized ring, smoothly undergoes indolization. The structures of type 16a aminals - besides the all-H parent mainly the diastereoisomeric 12,13-dicarboxylic esters and 13-carbonitriles - were clarified by X-ray and NMR analyses as well as by conversions. The pentacyclic aminals form a rigid bowl; the boat vs. chair conformation of the hydropyrimidine ring C is discussed.
View MoreAUSHUN PHARMACEUTICAL TECHNOLOGY CO,.LTD
Contact:+86-25-86883560 15951806178
Address:14 Dayingbi, Zhujiang Rd. East, Nanjing, Jiangsu, China.
ShangHai Ruiyi Medical Technology Co.,Ltd.
Contact:+86-21-54718086
Address:No951 Jianchuan RD,Minhang District
Zouping Fuhai Technology Development Co., Ltd.
Contact:+0532-86934525 18660293207
Address:jiuhu town industrial park Zouping County,bingzhou Provincejiuhu town industrial park
Shanghai Yuanye Bio-Technology Co., Ltd.
website:http://www.shyuanye.com
Contact:+86-21-61845781
Address:Building 6, No. 465, Changta Road,Songjiang District,Shanghai,China
Contact:+86-518-81061113
Address:No. 8 Lingzhou Road, Lianyungang, Jiangsu, China
Doi:10.1002/cmdc.201700243
(2017)Doi:10.1021/acs.orglett.8b01960
(2018)Doi:10.1021/ja513166w
(2015)Doi:10.1021/jo980003i
(1998)Doi:10.1039/c2ob25222h
(2012)Doi:10.1021/om980167p
(1998)