Authors
Advisor(s)
Abstract(s)
Acylation of antimalarial and bacteriostatic sulfonamides with N-protected amino acids and peptides was carried out using standard peptide coupling methods. These acylation reactions are regioselective for the N-4 nitrogen atom of diazine-containing sulfonamides. In contrast, only N-1 coupling was found for sulfisoxazole, an isoxazole-based sulfonamide. Computational studies suggest that a combination of geometrical, thermodynamic and electronic factors are responsible for the different reactivities reported. (C) 2003 Elsevier Ltd. All rights reserved.
Description
Keywords
Chemistry, Organic
Pedagogical Context
Citation
TETRAHEDRON. - Vol. 59, n. 38 (SEP 15 2003), p. 7473-7480
Publisher
PERGAMON-ELSEVIER SCIENCE LTD