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Synthesis of dibromodibenzo[d,g][1,3,6,2]dioxathiaphosphocin 6-sulfides

✍ Scribed by M. F. Stephen Babu; M. Anil Kumar; K. Srinivasulu; C. Suresh Reddy; M. Reddi Kumar

Publisher
Journal of Heterocyclic Chemistry
Year
2006
Tongue
English
Weight
81 KB
Volume
43
Category
Article
ISSN
0022-152X

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✦ Synopsis

Synthesis of 6-subsituted-2,10-dibromodibenzo [d,g][1,3,6,2]dioxathiaphosphocin 6-sulfides (3a-l) has been accomplished in a two-step process. Reaction of 5,5'-dibromo-2,2'-dihydroxydiphenyl sulfide 1 and thiophosphoryl chloride in equimolar quantities in the presence of triethylamine as a base and DMAP as a catalyst in anhydrous toluene afforded the intermediate 6-chloro-2,10-dibromodibenzo[d,g][1,3,6,2]dioxathiaphosphocin 6-sulfide 2. Subsequent reaction of the monochloride 2 with sodium phenoxides/ thiophenoxides afforded the title compounds. All the compounds showed moderate activity against bacteria and fungi.

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## Abstract Novel 6‐substituted 2,10‐dichloro‐4,8‐dinitrodibenzo[__d,g__][1,3,6,2]dioxathiaphosphocin‐6‐oxides **4** were synthesized by reacting 5,5′‐dichloro‐3,3′‐dinitro‐2,2′‐dihydroxydiphenyl sulfide (**2**) with different aryl phosphorodichloridates, trichloromethylphosphonic dichloride and O‐