A novel synthesis of 1,3 Thiazetidine‐2‐one and 1,3‐Oxazine‐2‐one Derivatives

Abstract

In the reactions of acetylthioacetanilides (1a–c) and diacetylthioacetanilides (3a–f) with phosgene 1,3‐thiazetidine‐2‐one (2a–c) and 1,3‐oxazine‐2‐one (5a–f) were obtained respectively. The structures of new compounds were elucidated by elemental analyses, i.r., 1H‐n.m.r., m.s., for 1d–f by 19F‐n.m.r. and for 2a and 5a by 13C‐n.m.r. spectral data.

Phase transfer catalysed alkylation of enamines of β‐keto carbothionic acid anilides with dihalogenoalkanes: Synthesis of Cyclic S,N‐Acetals of α‐Oxo Ketene

“…On the basis of analytical and spectral data we found that 8 underwent regiospecific S,N alkylation and this process was accompanied by hydrolysis of enamines to keto derivatives (Scheme 3). Some of the compounds obtained were found to be identical with those reported recently [8] and obtained by alkylation of benzoylthioacetanilide. Considering the result of the alkylation of enamines 8, we rulled out their preliminary hydrolysis to keto compounds and their further alkylation on the basis of following experimental data.…”

Spectroscopic study of the keto-enol equilibrium of N-aryldiacetylthioacetamides and their reactivity

“…Compounds 1a-f and 2a-f were prepared according to [11] and [10], respectively. X-Ray investigation.…”

“…In our previous investigation [10], with such double acylating reagent as phosgene, 1,3-oxazine derivatives 2 were isolated as the result of O-and N-acylation of N-aryldiacetylthioacetamides 1. However, a different course of reaction was observed when oxalyl chloride was used.…”

Polycarbonyl heterocyclics. [V]. Synthesis of pyrrolo[3,4‐c]pyridine and Furo[3,4‐c]‐pyridine derivatives by the Ring Transformation of Thiazolidine‐4‐on Derivatives

“…Acid treatment results in a cyclic lactone, and in rearrangement of thiopyrane derivatives to a thermodynamically more stable pyridine ring, due to which a derivative of furo [3.4- Compounds 2 a-d mere obtained according to [2] based on the Knoevenagel reaction of 2-(aroylmethylidene)-3-aryl thiazolidine-4.5-dione 1 a-d with malononitrile in ethanol a t 60°C.…”