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Combinatorial approaches to harmacophoric heterocycles: A solid‐phase synthesis of 3,1‐benzoxazine‐4‐ones
Author(s) -
Gordeev Mikhail F.
Publication year - 1998
Publication title -
biotechnology and bioengineering
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.136
H-Index - 189
eISSN - 1097-0290
pISSN - 0006-3592
DOI - 10.1002/(sici)1097-0290(199824)61:1<13::aid-bit5>3.0.co;2-1
Subject(s) - combinatorial chemistry , chemistry , reagent , solid phase synthesis , combinatorial synthesis , scope (computer science) , organic chemistry , urea , stereochemistry , biochemistry , computer science , peptide , programming language
An efficient solid‐phase synthesis of 3,1‐benzoxazine‐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‐4‐ones 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. © 1998 John Wiley & Sons, Inc. Biotechnol Bioeng (Comb Chem) 61:13–16, 1998.