Generation of oxindole-2-thiones (thiols) via dilithiatedN-tert-Boc-anilines. Synthesis of a sulfur analog of MK886-Reference-Cited by-同舟云学术

Generation of oxindole-2-thiones (thiols) via dilithiatedN-tert-Boc-anilines. Synthesis of a sulfur analog of MK886

Published:1995-03-01 Issue:3 Volume:73 Page:336-342
ISSN:0008-4042
Container-title:Canadian Journal of Chemistry
language:en
Short-container-title:Can. J. Chem.

Author:

Cervantes Alicia,Contreras Claudia A.,Guzman Angel,Vale Elena E.,Velarde Esperanza,Berthiaume Sylvie L.,Muchowski Joseph M.

Abstract

The N,C-dilithiated derivatives of the N-tert-butoxycarbonyl-2-alkylthiomethylanilines 5a–c and the N-tert-butoxycarbonyl-2-alkoxycarbonylmethylanilines 11a, b were converted into the N-tert-butoxycarbonyl-oxindole-2-thiones(thiols) 7a–c and 14a, b, respectively, by sequential reaction with carbon disulfide and methyl iodide. Compound 7b was converted into 10d, the sulfur analog of MK886. Keywords: N-tert-butoxycarbonyl-2-alkylthiomethylanilines, dilithiation, N-tert-butoxycarbonyl-2-alkoxycarbonylmethylanilines, N-tert-butoxycarbonyloxindole-2-thiones.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

Link

http://www.nrcresearchpress.com/doi/pdf/10.1139/v95-045

Reference7 articles.

1. MK886, a potent and specific leukotriene biosynthesis inhibitor blocks and reverses the membrane association of 5-lipoxygenase in ionophore-challenged leukocytes.

2. Ortho functionalization of N-(tert-butoxycarbonyl)aniline

3. Directed ortho lithiation of phenylcarbamic acid 1,1-dimethylethyl ester (N-BOC-aniline). Revision and improvements

4. Synthesis of quinolines via ortho-lithiated N-acylanilines. A modified Friedlaender synthesis

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