Domino reactions of 1,2-diimidoyl-1,2-dichloroethanes. Synthesis of 3-imino-1,2-dithia-3h-cyclopent-4-enes, 3-amino-2-thioxo-2,5H-pyrrol-5-ones, 2,3-diamino-4-thioxo-4H-thiopyrans, and 6-imino-6H-1,3-oxazines

The Journal of Organic Chemistry
Esen BellurP Langer

Abstract

The reaction of mono- and dilithiated ethyl thioglycolate with 1,2-diimidoyl-1,2-dichloroethanes, aza-analogues of oxalyl chloride, afforded (depending on the reaction conditions) 3-imino-1,2-dithia-3H-cyclopent-4-enes, 3-amino-2-thioxo-2,5H-pyrrol-5-ones, and 2,3-diamino-4-thioxo-4H-thiopyrans. The reaction of the dianion of ethyl hippurate with 1,2-diimidoyl-1,2-dichloroethanes afforded 6-imino-6H-1,3-oxazines.

References

Feb 1, 1989·The Journal of Antibiotics·M HaraH Nakano
Nov 18, 2000·Chemical Research in Toxicology·K S Gates
Apr 24, 2003·Journal of the American Chemical Society·Tonika ChatterjiKent S Gates
Sep 9, 2004·Chemical Reviews·Peter Langer, Walter Freiberg

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Citations

Jul 29, 2010·Chemistry, an Asian Journal·Pazhamalai AnbarasanMatthias Beller

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