Rearrangement of n-substituted 1-thiocarbamylazetidines into derivatives of 2-amino-3,4,5,6-tetrahydro-1,3-thiazine

✍ Scribed by M. Tišler

• Publisher: Elsevier Science
• Year: 1959
• Tongue: French
• Weight: 143 KB
• Volume: 1
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)99435-3

✦ Synopsis

TBE rearrangement of N-substituted 1-thiooarbamylasiridinea into derivatives of 2-amino-2-thiazoline is well known. 1,293 It was of interest to prepare some hitherto unknown related compounds with four-membered rings and to investigate their behaviour under conditions applied for rearrangement of threeambered rings. The N-substituted (mainly aryl) 1-thiocarbamylazetidines (I) were prepared from azetidine4 and the corresponding isothiocyanatee. Thus the following substances (I) were prepared: R: phenyl-, m.p. 112' (lit.4 gives m.p. llO"), R: p-tolyl-, m.p. 144-5', R: 2',4'-dimethylphenyl-, m.p. 167', R: pethoqphenyl-, m.p. 120°, R: m-chlorophenyl-, m.p. 112' and R: p-chlorophenyl-, m.p. 146-7'. These oompounde, when heated for 15 min with excess cont. hydrochloric ' S. Gabriel end R. Stelzner, Ber. 2g, 2929 (lS95).