Chemical studies of chromanone-thiadiazole, pyridazine and thiosulfin hybrid

Abstract

3-Chlorochromanon derivatives 4a,b are reacted with hydrazine hydrate to afford 3-hydrazino-2-tetrahydro(pyran or thiopyran)chroman-4-ones 5a,b. Then compound 5a,b is reacted with carbon disulfide and acetylacetone to give 5'-thiolo - 2-tetrahydro(pyrane or thiopyran)- spiro[chroman-3,2'- [1,3,4]-thiadiazole]-4-one 6a,b and 3', 5'-dimethyl- 2-tetrahydro(pyran or thiopyran) spiro [chroman-3,2'- piprazine]-4-one 7a,b, respectively. α-Chlorosulfenyl chlorides 2a,b are treated with thioacetic acid to form α-chloroalkyl disulfides 8a,b, the latter compounds 8a,b were treated with morpholine to furnish a mixture of 1,3,4-oxadithiins 9a,b, 1,3,4,5,6-oxatetrathiocins 10a,b, 1,2,4-trithiolanes 11a,b (cis- and trans-), 1,2,4,5-tetrathiins (cis- and trans-) 12a,b. The formation of the new compounds are confirmed by spectral (IR, ¹H NMR, and MS) analysis.