Solid-phase synthesis of trisubstituted 2,5-dihydrobenzo[f][1,2,5]thiadiazepine 1,1-dioxide derivatives

ACS Comb Sci. 2014 Aug 11;16(8):412-20. doi: 10.1021/co500084k. Epub 2014 Jun 12.

Abstract

The solid-phase synthesis of trisubstituted 2,5-dihydrobenzo[f][1,2,5]thiadiazepine 1,1-dioxides is reported. Acyclic polymer-supported intermediates were prepared using commercially available building blocks: Fmoc-protected amino acids, 2-nitrobenzenesulfonyl chlorides, and bromoketones. The acyclic precursors underwent acid-mediated release from the resin and the cyclization was completed in solution.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry
  • Benzene Derivatives / chemical synthesis*
  • Benzene Derivatives / chemistry
  • Chlorides / chemistry
  • Cyclization
  • Fluorenes / chemistry
  • Halogenation
  • Ketones / chemistry
  • Nitrobenzenes / chemistry
  • Oxides / chemical synthesis
  • Oxides / chemistry
  • Solid-Phase Synthesis Techniques / methods*
  • Thiazepines / chemical synthesis*
  • Thiazepines / chemistry

Substances

  • Amino Acids
  • Benzene Derivatives
  • Chlorides
  • Fluorenes
  • Ketones
  • N(alpha)-fluorenylmethyloxycarbonylamino acids
  • Nitrobenzenes
  • Oxides
  • Thiazepines
  • nitrobenzene