Can I read Synthesis of thiazino[6,5-b]indole derivatives, analogues of the phytoalexin cyclobrassinin. A new method for preparation of 3-aminomethylindole on EtoBox?

Synthesis of thiazino[6,5-b]indole derivatives, analogues of the phytoalexin cyclobrassinin. A new method for preparation of 3-aminomethylindole by Péter Csomós; Lajos Fodor; Pál Sohár; Gábor Bernáth is a Chemistry article available to read on EtoBox.

What is Synthesis of thiazino[6,5-b]indole derivatives, analogues of the phytoalexin cyclobrassinin. A new method for preparation of 3-aminomethylindole about?

An efficient non-reductive synthesis of 3-aminomethylindole (6) was developed from gramine (1) via 3-phthalimidomethylindole (2). The reactions of amine 6 with substituted methyl dithiobenzoates gave 3-(arylthiocarbonylaminomethyl)indoles. The Hugerschoff ringclosure reactions of the thiobenzamide intermediates (11a-f) with phenyltrimethylammonium tribromide and subsequent basic treatment furnished 2-arylthiazino[6,5-b]indole derivatives (14a-f). By use of the latter bromine source, the phytoalexin cyclobrassinin (8) was prepared in a considerably higher yield than described previously. The structures of the novel products were elucidated by IR, 1 H and 13 C NMR spectroscopy, including 2D-HMQC, 2D-HMBC and DEPT measurements.

Who reads Synthesis of thiazino[6,5-b]indole derivatives, analogues of the phytoalexin cyclobrassinin. A new method for preparation of 3-aminomethylindole?

Author

Péter Csomós; Lajos Fodor; Pál Sohár; Gábor Bernáth

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

2005

Language

EN

Field

Chemistry (Physical Sciences)