Complete ¹H and ¹³C NMR spectral assignment of benzo[d]isothiazole derivatives and of an isoindole isoster

Abstract

The complete (1)H and (13)C NMR assignments of the novel compound methyl 2-amino-3-(benzo[d]isothiazol-3-yl)propanoate (1), of 3-amino-5-methylbenzo[d]isothiazole (2) and N-(t-butyloxycarbonyl)-2-aminobenzo[d]isothiazol-3(2H)-one (3) and of the desulfurated isostere of 3, N-(t-butyloxycarbonyl)-2-aminoisoindolin-1-one (4), using 1D and 2D NMR techniques, including COSY, INADEQUATE, HSQC, and HMBC experiments are reported.

Benzisothiazolinone Derivatives as Potent Allosteric Monoacylglycerol Lipase Inhibitors That Functionally Mimic Sulfenylation of Regulatory Cysteines

“…The solvents were removed under reduced pressure, and the residue was purified by column chromatography (SiO 2 , hexane/AcOEt 70:30) to afford 31 (874.1 mg, 53%) as a white amorphous solid. Analytical data agree with those reported …”

“…Analytical data agree with those reported. 70 General Method G. To a cold (0 °C) solution of 31 in anhydrous DMF, KHMDS (1.2 equiv) was added in small portions. The reaction was stirred under a nitrogen atmosphere for 10 min, when a solution of the alkyl halide in anhydrous DMF was added.…”

Investigation of the Reaction between 3‐Benzisothiazolones, an Isoindole Isoster and Activated Acetylenes: Synthesis of Heterocyclic Backbones for Building Bioactive Molecules

“…2‐Aminobenzo[ d ]isothiazol‐3‐one ( 1 ) and benzo[ d ]isothiazol‐3‐one one ( 8 ) were synthesized as reported earlier by us . DBA was prepared according to , and 2‐aminoisoindolin‐1‐one ( 10 ) was synthesized following a modification of a described procedure . Unless otherwise noted, reagents were obtained from commercial suppliers and were used without purification.…”

“…A modification of a described procedure was used: to a magnetically stirred solution of N ‐( t ‐butyloxycarbonyl)‐2‐aminoisoindolin‐1‐one (0.10 g, 0.40 mmol) in ethyl acetate (10 mL) cooled at 0°C was added a solution of 3 M HCl in ethyl acetate (5 mL). The reaction mixture was then allowed to warm to room temperature and stirred overnight.…”