Simple synthesis of 3-acyl-5-alkyl(aryl)isoxazoles from terminal alkynes and nitrates of alkaline metals or ammonium-Reference-Cited by-同舟云学术

Simple synthesis of 3-acyl-5-alkyl(aryl)isoxazoles from terminal alkynes and nitrates of alkaline metals or ammonium

Published:2005-09-01 Issue:3 Volume:3 Page:370-376
ISSN:2391-5420
Container-title:Open Chemistry
language:
Short-container-title:

Author:

Rogachev Victor¹,Filimonov Victor¹,Kulmanakova Julya²,Yusubov Mehman²,Bender Wolfgang³

Affiliation:

1. 1Department of Organic Chemistry, Tomsk Polytechnic University, 634050, Tomsk, Russia

2. 2Department of Chemistry, Siberian State Medical University, 634050, Tomsk, Russia

3. 3Business Group Pharma, Research, Bayer AG, D-42096, Wuppertal, Germany

Abstract

AbstractA simple and general synthesis of 3-acyl-5-alkyl(aryl)isoxazoles by reaction of terminal alkynes with nitrates in acetic acid in the presence of SO3 or alkaline salts is described.

Publisher

Walter de Gruyter GmbH

Subject

Materials Chemistry,General Chemistry

Link

http://link.springer.com/content/pdf/10.2478/BF02479268.pdf

Reference12 articles.

1. V.O. Rogachev, M.S. Yusubov and V.D. Filimonov: “Reaction of phenylacetylene with sulfuric acid or sulfuric anhydride”, Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii), Vol. 35, (1999), pp. 415–418.

2. V.O. Rogachev, M.S. Yusubov, V.D. Filimonov and V.D. Ogorodnikov: “Unexpected formation of (E)-1-(methylthio)-1,2-diphenyl-2-chloroethene in reaction of diphenylacetylene with DMSO in the presence of sulfur trioxide and CCl4”, Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii), Vol. 36, (2000), pp. 290–291.

3. V.O. Rogachev, V.D. Filimonov and M.S. Yusubov: “A Novel Practical Reaction of Diarylalkyne With Sulfur Trioxide: Oxidation to 1,2-Diketones”, Synthesis, Vol. 7, (2001), pp. 1001–1003.

4. V.O. Rogachev, V.D. Filimonov and M.S. Yusubov: “New reaction of terminal acetylenes with nitrates in the presence of sulfur trioxide: heterocyclization into 3-acyl-5-aryl(alkyl)isoxazoles”, Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii), Vol. 37, (2001), pp. 1192–1193.

5. M.S. Yusubov, I.A. Perederina, V.D. Filimonov, T.-H. Park and K.-W. Chi: “A facile synthesis of α-iodo-β-nitroalkenes from alkynes using I2/NO3 or KI/NO3”, Synthetic Communications, Vol. 28, (1998), pp. 833–836.

Cited by 2 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Iron-Mediated Synthesis of Isoxazoles from Alkynes: Using Iron(III) Nitrate as a Nitration and Cyclization Reagent;The Journal of Organic Chemistry;2017-12-18

2. The reaction of alkynes with dimethyl sulfoxide, halogenated hydrocarbons and sulfur trioxide;Journal of Sulfur Chemistry;2008-10-01