83196-26-3Relevant academic research and scientific papers
Reaction of Organic Thiocyanates, Selenocyanates, and Cyanates with Malonyl Chloride
Ried, Walter,Nenninger, Jutta,Bats, Jan W.
, p. 1371 - 1382 (2007/10/02)
Organic thiocyanates and selenocyanates react with malonyl chloride to form the pyrano-oxazine-diones 1a, b, and 2a, b.Compound 4 is obtained in the case of phenacyl thiocyanate.With the exception of compound 6, nucleophilic substitution of the bromine atom in compound 1a is not possible.Excess n-propylamine leads to 7, while reaction in acidic medium gives 5.The reaction product of malonyl chloride and aromatic cyanates is strongly dependent on the reaction conditions.At temperatures up to +20 deg C, β-lactams 8a - g and hydrolysis products 9a - e, respectively,are formed.At 30 - 70 deg C substances 11a, d - f, at 60 - 90 deg C cyclization products 10a, d - g, and at temperatures of approx. 120 deg C decarboxylation products 12a, b, d are formed.An X-ray structural analysis is made of 9b.
Heterocyclic Synthesis with Malonyl Dichloride. Part 13. 6-Chloro-4-hydroxy-2-oxypyran-3-carboxanilides from N-Sulphinylanilines and Further Reactions of Malonyl Dichloride with Thiocyanates
Al-Ajely, Mohammed S.,Al-Rawi, Jasim M. A.,Elvidge, John A.
, p. 1575 - 1578 (2007/10/02)
N-Sulphinylanilines react with malonyl dichloride to give 6-chloro-4-hydroxy-2-oxopyran-3-carboxanilides with loss of the sulphoxide moiety as thionyl chloride.Milder conditions and electron-withdrawing substituents do not alter the course of the reaction of thiocyanates with malonyl dichloride to give 2-substituted-thio-7-chloro-4H,5H-pyranooxazine-4,5-diones.
