Base Mediated Reactions in Solid-Liquid Media. A 1,3-Dipolar Cycloaddition Route to Pyrrolines and Pyrroles from Imino Chlorosulfides.

DOI: 10.1016/S0040-4039(00)60030-8

Source and publish data:

Tetrahedron Letters p. 6155 - 6158 (1992)

Update date:2022-08-04

Topics:

Authors:

Berree, Fabienne

Marchand, Evelyne

Morel, Georges

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1016/S0040-4039(00)60030-8

Nitrile ylides, generated in basic conditions (HCl abstraction) from N- and N-imino chlorosulfides, undergo 1,3-dipolar cycloadditions with electron-deficient dipolarophiles to produce pyrroles and pyrrolines.Heterogeneous media are found to furnish the best conditions for these reactions.One pyrrole can also be prepared from methyl N- chlorothioimidate and dimethyl acetylenedicarboxylate on alumina-potassium fluoride mixture as solid support, under microwave irradiation. Key words: Imino chlorosulfides; alumina-dispersed potassium fluoride and potassium hydroxide; 1,3-dipolar cycloaddition; pyrroles.

Full text of DOI:10.1016/S0040-4039(00)60030-8

Products guided by the article

Product name:2-Methylsulfanyl-1H-pyrrole-3-carboxylic acid methyl ester

Cas No:144878-82-0

R&D Labs maybe for 144878-82-0

Hangzhou Dingyan Chem Co., Ltd

website:http://www.dingyanchem.com

Contact:86-571-87157530-8002

Address:RM.1118,NO.1 Building, Baiyun Tower,Jianggan Area, Hangzhou city, China,310004
Suzhou Wedo Chemicals Co., Ltd.

Contact:86 512 58100425

Address:Zonger Road, DongSha Industry Park , Zhangjiagang, Jiangsu, China
Sinonine Industry Co.,Ltd

Contact:86+21-56421993

Address:3F,BUILDING 10,NO.2889 JINKE ROAD, SHANGHAI.
Beijing Century Richap Chemistry Co.,Ltd

Contact:+86- 010-64455497

Address:Guannan County, Lianyungang City, Jiangsu Province, China
ShangHai BMG Chemical Co., Ltd

Contact:+86-13524845543

Address:Room 602, no 291 sikai road shanghai

Relevant to this article

Synthesis of amphotericin B. I. Fragment A of the aglycon

Doi:10.1021/jo00189a046
(1984)
Microwave assisted efficient aminocarbonylation of N-tosylhydrazones with molybdenum hexacarbonyl and amines

Doi:10.1016/j.tetlet.2013.07.149
(2013)
Total synthesis of emericellamides A and B

Doi:10.1016/j.tetasy.2013.07.012
(2013)
Highly stereoselective transformation of (1S,3S)-cis-1,3-disubstituted tetrahydro-β-carbolines into (1S,3R)-trans-1,3-disubstituted tetrahydro-β-carbolines: An improved asymmetric synthesis of tadalafil from l-tryptophan

Doi:10.1016/j.tetasy.2013.06.006
(2013)
Chiral bifunctional squaramide catalyzed asymmetric tandem Michael-cyclization reaction: Efficient synthesis of optically active 2-amino-4H-chromene-3-carbonitrile derivatives

Doi:10.1016/j.tetasy.2013.07.010
(2013)
Optimization of Novel 1-Methyl-1 H-Pyrazole-5-carboxamides Leads to High Potency Larval Development Inhibitors of the Barber's Pole Worm

Doi:10.1021/acs.jmedchem.8b01544
(2018)

Article Doi