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 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.
Bellur
Esen
E
Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany.
Görls
Helmar
H
Langer
Peter
P
D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D004000:Dichloroethylenes / Q000737:chemistry*; D005025:Ethylene Dichlorides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D003517:Cyclopentanes; D004000:Dichloroethylenes; D005025:Ethylene Dichlorides; D010078:Oxazines; D011714:Pyrans