Synthesis and conformational analysis of dibenzodithiocin derivatives

✍ Scribed by P. Sohár; I. Kövesdi; J. Szabó; Á. Katócs; L. Fodor; E. Szücs; G. Bernáth; J. Tamás

• Publisher: John Wiley and Sons
• Year: 1989
• Tongue: English
• Weight: 653 KB
• Volume: 27
• Category: Article
• ISSN: 0749-1581
• DOI: 10.1002/mrc.1260270809

✦ Synopsis

N-(3,4-Dialkoxyphenylthiomethyl)aroylamides (la, b) reacted with phosphoryl chloride to give not only the expected 4H-and 2H-l,34enzothiazine derivatives (4a, b and Sa, b), but also dibenzodithiocins of new (dibenzo(d,g][1,3]dithiocins 2a, b) and known (dibenzo(b,f][l,S]dithiocins 3a, b) types. The analogous reaction of the 4-methylaroylamide 8a furnished the 4H-1,Sbenzothiazine 9a, the dibenzo(b,f][l,5]dithiocin derivative 1Oa and benzonitrile. In contrast, 8b (the chloro analogue of 8a) furnished only benzonitrile and bis(4-chloropheny1mercapto)methane ( 11). The structures of the new compounds were confirmed by IR, 'H and "C NMR, and (in part) by mass spectrometry. Temperaturedependent 'H NMR studies were used for the conformational analysis of 2a and its disulphone 6a; the nature and free enthalpies of activation of the two different conformational motions occurring at higher temperatures were determined.