ISSN:
0941-1216
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Synthesis and Reactions of 2-Mercapto-6-thioxo-thiopyran-3-carboxylate derivatives6-Amino-thiopyran-2-thiones (1) react with dihydrogen sulfide in the presence of pyridine and triethyl amine to yield 6-thioxo-thiopyran-2-thiolates (2). Methylation of 2 gives the methylthio compounds 3 and 4. Further methylation of 3a and 4a yields the thiapyrylium salt (7). The reaction of 2-imino-thiopyran (6) with carbon disulfide represents another route to the 6-methylthio-thiopyran-2-thione (4a). The 2-methylthio-thiopyran-6-thione (3a) undergoes substitution of the methylthio group with amines to 8 or reacts with phenylhydrazine to phenylhydrazono-thiopyrane (9c). 6-Thioxo-thiophen-2-thiolates (2a,b) react with hydrazine hydrate to give hydrazono-thiopyranes (10a,b) which can be S-methylated. On the contrary 2c gives with hydrazine hydrate under ring transformation the pyridine-2-thiolate (11). N,S-Acetals (12) and 1,3,4-thiadiazoles (15), which give rise to new pyridine derivatives (14) and (17), can be obtained from 1-Amino-pyridin-2-thiolate (11).
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19963380198
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