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Regioselective N ‐alkylation of 1,2,6‐thiadiazine 1,1‐dioxide derivatives
Author(s) -
Goya P.,
Martínez P.,
Ochoa C.,
Stud M.
Publication year - 1981
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570180304
Subject(s) - chemistry , diazomethane , regioselectivity , alkylation , dimethyl sulfate , reactivity (psychology) , nitro , medicinal chemistry , ion , methylation , selectivity , organic chemistry , medicine , biochemistry , alkyl , alternative medicine , pathology , gene , catalysis
Reactivity towards alkylating agents in relation to the capacity to bind sodium ions of 1,2,6‐thiadiazine 1,1‐dioxide derivatives is described. The compounds studied are: 1 , 4‐nitro‐, 2 , 4‐cyano‐, 3 ,4‐ethoxycarbonyl‐2 H ,6 H ‐1,2,6‐thiadiazin‐3‐one 1,1‐dioxide and 4 , 3‐amino‐4‐cyano‐6 H ‐1,2,6‐thiadiazine 1,1‐dioxide. Methylation with dimethyl sulfate of 4‐nitro‐ and 4‐cyanothiadiazines 1 and 2 , which show the capacity to bind sodium ions, takes place regioselectively at position 2, whilst the thiadiazines which lack this feature ( 3 and 4 ) are methylated at 2 and 6, and 6 respectively. On using diazomethane, in the absence of alkaline ions, no selectivity was observed. Glycosidation reactions of 1, 3 and 4 have also been carried out. The structure of the newly synthesized compounds are discussed on the basis of their analytical and spectroscopic data.