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Combinatorial approaches to harmacophoric heterocycles: A solid-phase synthesis of 3,1-benzoxazine-4-ones

✍ Scribed by Mikhail F. Gordeev

Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 183 KB
Volume: 61
Category: Article
ISSN: 0006-3592
DOI: 10.1002/(sici)1097-0290(199824)61:1<13::aid-bit5>3.0.co;2-1

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✦ Synopsis

An efficient solid-phase synthesis of 3,1benzoxazine-4-ones is described. Immobilized amino acid based functionalized urea derivatives 2 undergo a high yielding heterocyclization under mild conditions in presence of coupling reagents (DIC, TsCl/Py, or Ac 2 O) to afford 3,1-benzoxazine-4ones 6. The method offers broad scope for structural and chemical diversity, and is amenable for combinatorial synthesis of 3,1-benzoxazine-4-ones libraries with potential for discovery of novel serine protease inhibitors.

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