Regiospecificty in the heterocyclization of β-oxonitriles to 5-substituted 4-oxothiazolidine derivatives

Journal of the Serbian Chemical Society

Džambaski Zdravko D.¹  Stojanović Milovan¹  Marković Rade²  Baranac Marija M.²  Steel Peter³ 

[1] Center for Chemistry ICTM, P. O. Box 815, 11000 Belgrade, Serbia and Montenegro;Faculty of Chemistry, University of Belgrade, Studentski trg 16, P. O. Box 158, 11001 Belgrade, Serbia and Montenegro;University of Canterbury, P. O. Box 4800, Christchurch, New Zealand;

关键词: regiospecific;    heterocyclization;    4-oxothiazolidines.;   

DOI  :  10.2298/JSC0305383M

来源: DOAJ

【 摘 要 】

Astudy on the regiospecificity of the base-catalyzed reaction of activated β-oxonitriles 1 with diethyl mercaptosuccinate affording the title compounds 3 is reported. Other competitive heterocyclic products, that is 4-oxo-1,3-thiazinanes 4, derivatives of tetrahydrothiophene 5 and/or thiacyclohexane 6 which on the grounds of mechanistic considerations could be formed, were not observed. Spectroscopic and experimental evidence together with theoretical considerations, provides a reasonable explanation for the observed regiospecificity.

【 授权许可】

Unknown