Synthesis and conformational analysis of dibenzodithiocin derivatives

P. Sohár, I. Kövesdi, J. Szabó, Katócs, L. Fodor, E. Szücs, G. Bernáth, J. Tamás

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Abstract

N‐(3,4‐Dialkoxyphenylthiomethyl)aroylamides (la, b) reacted with phosphoryl chloride to give not only the expected 4H‐ and 2H‐1,3‐benzothiazine derivatives (4a, b and 5a, b), but also dibenzodithiocins of new (dibenzo[d,g][1,3]dithiocins 2a, b) and known (dibenzo[b,f][1,5]dithiocins 3a, b) types. The analogous reaction of the 4‐methylaroylamide 8a furnished the 4H‐1,3‐benzothiazine 9a, the dibenzo[b, f][1,5]dithiocin derivative 10a and benzonitrile. In contrast, 8b (the chloro analogue of 8a) furnished only benzonitrile and bis(4‐chlorophenylmercapto)methane (11). The structures of the new compounds were confirmed by IR, 1H and 13C NMR, and (in part) by mass spectrometry. Temperature‐dependent 1H 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.

Original languageEnglish
Pages (from-to)760-766
Number of pages7
JournalMagnetic Resonance in Chemistry
Volume27
Issue number8
DOIs
Publication statusPublished - 1989

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Keywords

  • H and C NMR
  • Conformation
  • Dibenzodithiocins
  • Structural isomerism
  • Synthesis

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)

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