Regioselective reduction of 3-substituted 2,3-dihydrobenzothiadiazines with borohydrides

Tetrahedron Letters

Volumn 51, Issue 33, 2010, Pages 4433-4436

  Battisti, Umberto M ^a   Cannazza, Giuseppe ^a   Carrozzo, Marina M ^a   Braghiroli, Daniela ^a   Parenti, Carlo ^a   Rosato, Francesca ^b   Troisi, Luigino ^b  

^a UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

^b UNIVERSITY OF SALENTO   (Italy)

Author keywords

2 Aminobenzenesulfonamide; 3 Chiral 2,3 dihydrobenzothiadiazines; Reduction; Sodium cyanoborohydride

Indexed keywords

2 AMINO 5 CHLORO N ETHYLBENZENESULFONAMIDE; 5 CHLORO 2 ETHYLAMINO)BENZENESULFONAMIDE; BENZENESULFONAMIDE DERIVATIVE; CYANOBOROHYDRIDE SODIUM; SODIUM BOROHYDRIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SUBSTITUTION; PH MEASUREMENT; TEMPERATURE SENSITIVITY;

EID: 77955424648     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.06.081     Document Type: Article

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12. 3CN (6.0 mmol) was added. The resulting mixture was stirred at room temperature for 3 h. The mixture was then neutralized with NaOH 10 M and extracted with ethyl acetate (2 × 20 ml). The organic layer was washed with deionized water and dried over anhydrous sodium sulfate. The solvent was removed under vacuum and the residue was purified by chromatography, eluting with diethyl ether/petroleum ether 1:1, to give the pure product.
13. 3CN (6.0 mmol) was added to a solution of 7-chloro-3-methyl-3,4-dihydro-2H-1,2,4 benzothiadiazine-1,1-dioxide (1.0 mmol) in 30% aqueous ethanol (20 ml). The mixture was stirred at 70 °C for 6 h. The mixture was neutralized with dil HCl and extracted with ethyl acetate (2 × 20). The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under vacuum. The residue was purified by column chromatography using diethyl ether/petroleum ether 1:1, to give the pure product.