Journal
TETRAHEDRON LETTERS
Volume 42, Issue 1, Pages 109-111Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(00)01896-7
Keywords
solid-phase synthesis; benzothiazole; 2,3-dihydro-[1,5]-benzothiazepine
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Bis-(2-nitro-4-carboxyphenyl) disulfide was loaded on Wang resin and Rink amide resin. The nitro group was reduced to its amine with concomitant cleavage of the disulfide bond using SnCl2.H2O to afford 2. Condensation of an aldehyde and nucleophilic attack on an alpha,beta -unsaturated ketone, followed by TFA cleavage from the resin, gave benzothiazole 3 and 2,3-dihydro-[1,5]-benzothiazepine 4, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.
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