Reactions of o-aminothiophenol and o-aminophenyl disulfide with itaconic anhydride and (-)-dimenthyl itaconate: access to enantiomerically pure 1,5-benzothiazepines and benzothiazolyl-2-methylacrylic acid
| Title | Reactions of o-aminothiophenol and o-aminophenyl disulfide with itaconic anhydride and (-)-dimenthyl itaconate: access to enantiomerically pure 1,5-benzothiazepines and benzothiazolyl-2-methylacrylic acid |
| Publication Type | Journal Article |
| Year of Publication | 2007 |
| Authors | Baag, MMerajuddin, Sahoo, MKumar, Puranik, VG, Argade, NP |
| Journal | Synthesis-Stuttgart |
| Issue | 3 |
| Pagination | 457-463 |
| Date Published | FEB |
| Type of Article | Article |
| ISSN | 0936-5214 |
| Keywords | Magnetic nanoparticles, magnetic properties, spin glasses |
| Abstract | {A facile chemo- and regioselective reactions of o-aminothiophenol (o-ATP) with itaconic anhydride is described. 1,5-Benzothiazepinyl-3-acetic acid is obtained in 81% yield via the exclusive Michael type addition of the thiol unit from o-ATP to the carbon-carbon double bond in itaconic anhydride followed by an intramolecular anhydride ring opening with an amine unit. The moderately stereoselective Michael type addition of the thiol unit from o-ATP to (-)-dimenthyl itaconate to obtain a mixture of diastereomers in a 7:3 ratio in 82% yield has been demonstrated. The reductive sulfur-sulfur bond cleavage in the dicarboxylic acid, 2({2-[2-(3-carboxybut-3-enoylamino)phenyidisulfanyl]phenylcarbamoyl\ |
| DOI | 10.1055/s-2006-958977 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.652 |
Divison category:
Center for Material Characterization (CMC)
Organic Chemistry
Physical and Materials Chemistry