N. Gautam, Rajni Gupta, D. Gautam
2000
Citations
0
Influential Citations
12
Citations
Journal
Heterocyclic Communications
Abstract
Synthesis of 3-bromo-l-methyl phenothiazines is prepared by the Smiles rearrangement of 5-bromo-2-formamido-3-methyI-2'-nitro -4'-substituted diphenyl sulfides. The formyl derivatives were prepared by the formylation of the resultant diphenyl sulfides obtained by the condensation of2-amino-5-bromo-3-methylbenzenethiol with σ-halonitrobenzene in ethanolic acetate solution. However, halonitrobenzenes containing a nitro group at both ortho positions to the reactive halogen atom on condensation with 2-amino-5-bromo-3-methylbenzenethiol directly yielded 9nitrophenothiazine as Smiles rearrangement and ring closure occur simultaneously in situ due to combined resonance and inductive effects reinforced by two nitro groups. The IR, NMR and Mass-spectral studies are also included.