Acylation and alkoxycarbonylation of benzoxazoline-2-thione and benzothiazoline-2-thione
Acylation of benzoxazoline-2-thione (1) and benzothiazoline-2-thione (2) with acetic anhydride (3) and acyl chlorides (4) gave N-acyl (5, 6) and/or S-acyl (7, 8) derivatives depending on the nature of acylating agents and bases used. Alkoxycarbonylation of 1 with aralkyl chlorocarbonates (9) gave N-alkoxycarbonyl derivatives (10) mainly, while that of 2 with aralkyl chloroccarbonates (9) gave S-alkoxycarbonyl derivatives (12) exclusively. Photolysis of N-acyl derivatives (5 or 6) in the presence of alcohols afforded 1 or 2, respectively, together with esters (16).
Nishio, Takehiko,Shiwa, Kiyoko
p. 313 - 324
(2007/10/03)
On the Use of Five-Membered Heterocycles in Peptide Chemistry
N-Acyl derivatives of 2-benzoxazolethiol, 2-benzothiazolethiol and 2-benzimidazolethiol are proposed for use both as efficient acylating agents for the synthesis of N-benzyloxycarbonyl and N-fluorenylmethyloxycarbonyl amino acid derivatives and as activated amides for the synthesis of peptides.
Romani, S.,Moroder, L.,Bovermann, G.,Wuensch, E.
p. 738 - 742
(2007/10/02)
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