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Two-step conversion of 3,4,4,5-tetrachloro-4H-1,2,6-thiadiazine into 4,5,6-trichloropyrimidine-2-carbonitrile.
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Jun2017, Vol. 58 Issue 26, p2618-2621. 4p. - Publication Year :
- 2017
-
Abstract
- Tin reduction of 3,4,4,5-tetrachloro-4 H -1,2,6-thiadiazine afforded perchloro-9-thia-1,5,8,10-tetraazaspiro[5.5]undeca-1,4,7,10-tetraene (10%) and 3,5-dichloro-4 H -1,2,6-thiadiazine-4-thione (27%), the structures of which were supported by single crystal X-ray crystallography. Treating the tetrachlorothiadiazine with Ph 3 P (1 equiv.) afforded the corresponding spirocycle in a useful 66% yield, the degradation of which with BnEt 3 NCl (0.5 equiv.) afforded densely functionalized 4,5,6-trichloropyrimidine-2-carbonitrile in 81% yield. Rational mechanisms for the formation of products are proposed. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 58
- Issue :
- 26
- Database :
- Academic Search Index
- Journal :
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 123464160
- Full Text :
- https://doi.org/10.1016/j.tetlet.2017.05.082