1.
Chem Pharm Bull (Tokyo)
; 50(9): 1215-8, 2002 Sep.
Artigo
em Inglês
| MEDLINE
| ID: mdl-12237538
RESUMO
The synthesis of 3-amino-2-methoxycarbonyl-4,7-dimethoxybenzo[b]thiophene (5) and benzothieno[3,2-d][1,3]oxazin 15 from 3,6-dimethoxy-2-nitrobenzaldehyde (1) is reported. Benzo[b]thiophene-4,7-quinones 9 and 10 were prepared in good yields by oxidative deprotection of the corresponding dimethoxybenzothiophenes 8 and 7. Cycloaddition reaction of quinone 8 with 1-(E)-trimethylsilyloxy-1,3-butadiene followed by acid-induced aromatization provides access to naphtho[2,3-b]thiophene-4,9-quinone 13 and 14. The in vitro activity of the new quinones against Leishmania amazonensis and human-T-cell leukemia virus type 1 (HTLV-1) is reported.