Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 35, 2005 - Issue 6
148
Views
18
CrossRef citations to date
0
Altmetric
Original Articles

Microwave‐Assisted Generation and Reactions of Nitrile Sulfides

, &
Pages 807-813 | Published online: 20 Aug 2006

References

  • Paton , R. M. 1989 . The chemistry of nitrile sulfides . Chem. Soc. Rev. , 18 : 33 – 52 . For reviews of nitrile sulphide chemistry, see
  • Wentrup , C. and Kambouris , P. 1991 . Chem. Rev. , 91 : 363 – 373 .
  • Padwa , A. 1984 . 1,3‐Dipolar Cycloaddition Chemistry Edited by: Padwa , A. New York : Wiley . Chap. 2, 3
  • Howe , R. K. , Gruner , T. A. , Carter , L. G. , Black , L. L. and Franz , J. E. 1978 . Cycloaddition reactions of nitrile sulfides with acetylenic esters: Synthesis of isothiazolecarboxylates . J. Org. Chem. , 43 : 3736 – 3742 .
  • Sanders , M. J. , Dye , S. L. , Miller , A. G. and Grunwell , J. R. 1979 . 1,3‐Dipolar cycloaddition reactions of benzonitrile N‐sulfide . J. Org. Chem. , 44 : 510 – 513 .
  • Crosby , J. , Grant , K. J. , Greig , D. J. , Paton , R. M. , Rankin , J. G. and Ross , J. F. 2002 . Nitrile sulfides. Part 12: Generation of nitrile sulfides from 1,4,2‐dithiazol‐2‐ones . ARKIVOC , 3 : 121 – 129 . Chem. Abstr. 2003, 138, 287605
  • Crosby , J. , McKie , M. C. , Paton , R. M. and Ross , J. F. 2000 . A convenient route to 3‐substituted isothiazoles using nitrile sulfide cycloaddition chemistry . ARKIVOC , 1 ( 5 ) : 720 – 734 . Chem. Abstr. 2002, 136, 279373
  • Howe , R. K. and Franz , J. E. 1978 . Cycloaddition reactions of nitrile sulfides with olefins . J. Org. Chem. , 43 : 3742 – 3745 .
  • Howe , R. K. and Franz , J. E. 1974 . Nitrile sulfides: Synthesis of 1,2,4‐thiadiazoles . J. Org. Chem. , 39 : 962 – 964 .
  • Hogan , I. T. and Sainsbury , M. 1984 . The synthesis of dendrodoine, 5‐[3‐(N,N‐dimethylamino‐1,2,4‐thiadiazolyl]‐3‐indolylmethanone, a metabolite of the marine tunicate dendroda grossular . Tetrahedron , 40 : 681 – 682 .
  • Greig , D. J. , McPherson , M. , Paton , R. M. and Crosby , J. 1986 . Synthesis of 5‐trichloromethyl‐1,2,4‐thiadiazoles by 1,3‐dipolar cycloaddition of nitrile sulfides to trichloroacetonitrile . Phosphorus Sulfur Relat. Elem. , 26 : 151 – 154 .
  • Buffel , D. K. , Simons , B. P. , Deceuninck , J. A. and Hoornaert , G. J. 1991 . 3‐β‐D‐Ribofuranosyl‐1,2,4‐thiadiazole‐5‐carboxamide and 3‐β‐D‐ribofuranosylisothiazole‐5‐carboxamide: Preparation and synthetic applications of O‐benzoyl‐protected 2,5‐anhydro‐D‐allononitrile N‐sulfide . Nucleic Acid Chem. , 4 : 155 – 162 .
  • McKie , M. C. and Paton , R. M. 2002 . Nitrile sulfides, Part 13: Synthesis of 5‐acyl‐1,2,4‐thiadiazoles by cycloaddition of nitrile sulfides to acyl cyanides . ARKIVOC , 6 : 15 – 21 . Chem. Abstr. 2003, 138, 287606
  • Damas , A. M. , Gould , R. O. , Harding , M. M. , Paton , R. M. , Ross , J. F. and Crosby , J. 1981 . Nitrile sulfides, Part 1: 1,3‐Dipolar cycloaddition to carbonyl groups activated by trihaloalkyl substituents; synthesis and crystal structure of 1,3,4‐oxathiazoles . J. Chem. Soc., Perkin Trans. 1 , : 2991 – 2995 .
  • Wai , K.‐F. and Sammes , M. P. 1991 . Dithiazoles and related compounds, Part 3: Preparation of 5H‐1,4,2‐dithiazoles via 1,3‐dipolar cycloadditions between nitrile sulfides and thiocarbonyl compounds, and some conversions into 3,5‐diaryl‐1,4,2‐dithiazolium salts . J. Chem. Soc., Perkin Trans. 1 , : 183 – 187 .
  • Muehlbauer , E. and Weiss , W. 5‐Substituted‐1,3,4‐oxathiazol‐2‐ones . British Patent 1079 3438 . 1967 . Chem. Abstr. 1968, 68, 69000
  • Caddick , S. 1995 . Microwave assisted organic reactions . Tetrahedron , 51 : 10403 – 10432 .
  • Lidstrom , P. , Tierney , J. , Wathey , B. and Westman , J. 2001 . Microwave assisted organic synthesis—a review . Tetrahedron , 57 : 9225 – 9283 .
  • Touaux , B. , Klein , B. , Texier‐Boullet , F. and Hamelin , J. 1994 . Synthesis in dry media coupled with microwave irradiation; application to alkoxycarbonylformonitrile oxide generation and 1,3‐dipolar cycloaddition . J. Chem. Res., Synop. , : 116 – 117 .
  • Kaddar , H. , Hamelin , J. and Benhoua , H. 1999 . Microwave‐assisted 1,3‐dipolar cycloaddition reactions of nitrile imines and nitrile oxides . J. Chem. Res., Synop. , : 718 – 719 .
  • De la Cruz , P. , Diaz‐Ortiz , A. , Garcia , J. J. , Gomez‐Escalonilla , M. J. , de la Hoz , A. and Langa , F. 1999 . Synthesis of new C60‐donor dyads by reaction of pyranosyl hydrazones with [60]fullerene under microwave irradiation . Tetrahedron Lett. , 40 : 1587 – 1590 .
  • Krayushkin , M. M. , Kalik , M. A. and Kudryavtseva , A. Y. 1993 . Synthesis of 3‐thienyl‐substituted isothiazolines and 1,2,4‐thiadiazoles based on nitrile sulfides of the thiophene series . Russ. Chem. Bull. , : 1477 – 1481 .
  • Franz , J. E. and Black , L. L. 1970 . Thermolysis and photolysis of 1,3,4‐oxathiazol‐2‐ones . Tetrahedron Lett. , 16 : 1381 – 1384 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.