In:
Chemische Berichte, Wiley, Vol. 110, No. 3 ( 1977-03), p. 820-832
Abstract:
Cycloaddition Reactions of Heterocumulenes, IX. 1:1‐, 2:1‐, and 3:1‐Adducts from the Reaction of Isothiocyanates with 3‐Dimethylamino‐2,2‐dimethyl‐2 H ‐azirine Treatment of the azirine 1 with the activated isothiocyanates 2a, b leads to 1,3‐cleavage of the ring and formation of the dipoles 5 , which can be characterized by hydrolysis, protonation and methylation to give 6–8 . In the reaction of 1 with the sterically hindered alkyl isothiocyanates 2f–i the ring of 5 is split to form the carbodiimides 10. 10f–i hydrolyze via 5 to give the thioureas 11 , from which 11f, g easily cyclize to yield the 2‐thiohydantoins 12 . Cycloaddition reactions of 10f lead to the heterocycles 14, 15 , and 17 . The alkyl isothiocyanates 2c–e react with 1 , depending on the reaction conditions, to give the 3:1‐adducts 14 or the dipolar 2:1‐adducts 21 . The hydrolysis of 21e leads to the thiazolinone 26 with the acyclic product 25 as intermediate.
Type of Medium:
Online Resource
ISSN:
0009-2940
DOI:
10.1002/cber.19771100304
Language:
English
Publisher:
Wiley
Publication Date:
1977
detail.hit.zdb_id:
779-1