Journal of Organic Chemistry p. 4374 - 4378 (1984)
Update date:2022-08-04
Topics: Rearrangement Polyphosphoric acid Arylhydrazones α,β-Unsaturated Carbonyl Compounds Experimental
Fusco, Raffaello
Sannicolo, Franco
The reactions of a series of N-methyl-N-arylhydrazones of α,β-unsaturated carbonyl compounds 1 with hot polyphosphoric acid are described.Three main courses were observed, depending on the structure of the carbonyl portion of the substrate.Unsaturated α-oxo ester hydrazones (1a-c) rearranged to give substituted 3-<2-(methylamino)aryl>-2-oxo-3-butenoic acid esters (2a-c); the reaction mechanism strictly resembles the initial steps of the Fischer indole synthesis.Unsaturated aldehyde hydrazones alternatively gave either the di-3-indolylmethane derivatives (3a,b) or the amino nitriles (4a-c).The first process develops through intermediates structurally similar to 2; the latter was demonstrated to be exclusively intramolecular.
View MoreYangzhou Zhongbao Pharmaceutical Co.,Ltd
Contact:+86-514-88290838
Address:Jiangsu Baoying county economic develpment zone in baoying avenue91
QINGDAO NEW FLOURISH INTERNATIOANAL TRADE CO., LTD.
Contact:+86 532 80861829
Address:No. 1, Yinchuan East Road, 266061, Qingdao, China
Jinhua City Mingzhu Pharmaceutical Co.,Ltd.
Contact:15857995878 0579-82207761
Address:No.169 Shenze Road, New Area,Jinpan Development Zone, Jinhua
Wuhan Silworld Chemical Co.,Ltd
website:http://www.silworldchemical.com
Contact:+86-27-85613400
Address:No.198 jiangjun Road, Wuhan,China 430033
Guangzhou Flower's Song Fine Chemical CO,. Ltd
Contact:+86-20-87475199
Address:No.12, Fenghuang 3 Road, Jiulong Industrial Park, Luogang District, Guangzhou. China
Doi:10.1021/ol0624023
(2006)Doi:10.1021/ol062126s
(2006)Doi:10.1016/j.bmc.2006.07.055
(2006)Doi:10.1002/adsc.200900621
(2009)Doi:10.1016/j.tet.2006.09.031
(2006)Doi:10.1002/aoc.3706
(2017)