HETEROCYCLES

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■ Synthesis and Properties of Novel Medium-sized Heterocyclic Compounds Containing Two Sulfur Atoms in the Ring and Synthetic Approaches to Conjugated Cyclic Disulfonium Ylides

Hiroshi Shimizu,* Hiroyoshi Watanabe, Masahiro Mizuno, Tadashi Kataoka, and Mikio Hori

*Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan

Abstract

Tribenzo[b,f,h][1,4]dithiecin (8) was prepared by coupling 2,2’-bis(bromomethyl)biphenyl (10) with 1,2-benzenedithiol (11) in the presence of NaH in acetonitrile. Another novel dithiecin derivative, 1,8-dihydro-2,7-benzodithiecin (9) was synthesized by coupling of 1,4-dimercapto-2,3-O-isopropylidene-Lg-threitol (13a) with α,α’-dibromo-o-xylene (12), followed by hydrolysis and subsequent dehydration via the mesylate derivative (16). The benzodithiecin (9) was also prepared by treatment of dithiol (18) with butadiyne along with α,α’-bis(1-buten-3-ynylthio)-o-xylene (19) as a byproduct. Compound (19) was subjected to an intramolecular coupling reaction using CuCl-pyridine-O₂ in benzene to yield the 12-membered ring compound (23). We also describe our effort to prepare the corresponding cyclic diylide compounds from the above new dithiecins (8) and (9), and known dithiecin (7).