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Synlett 2022; 33(17): 1729-1732
DOI: 10.1055/a-1912-2293
DOI: 10.1055/a-1912-2293
letter
A Facile and Efficient One-Pot Procedure for the Synthesis of Novel 2-Substituted 3-Thioxoisoindolin-1-one Derivatives
Authors
We acknowledge the financial support from University of Tehran.
Abstract
In this paper, a novel and efficient method is reported for the synthesis of novel 2-substituted 3-thioxoisoindolin-1-one derivatives. The method is based on the solvent-free reaction of 2-carboxybenzaldehyde with aliphatic amines and sulfur at 100 °C. This reaction is intensely significant, especially in pharmacy applications, due to the facile synthesis of asymmetric thioxoisoindolin-1-one derivatives with phthalimide backbones.
Key words
3-thioxoisoindolin-1-one - sulfur containing compound - phthalimide - multicomponent reactionsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1912-2293.
- Supporting Information (PDF)
Publication History
Received: 17 May 2022
Accepted after revision: 28 July 2022
Accepted Manuscript online:
28 July 2022
Article published online:
14 September 2022
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- 27 General Procedure for the Synthesis of Compound 3a–k A mixture of 2-formylbenzoic acid (1, 1 mmol), aliphatic amine derivatives (2a, 1.2 equiv.), and S8 (2 equiv.) were added, and the mixture was stirred at 100 °C under solvent-free conditions for 3 h. When the reaction was completed (TLC), the mixture was cooled at r.t., and the residue was purified with column chromatography from n-hexane/EtOAc (3:1) to afford the compounds 3a–k in 57–86%. 2-Isopropyl-3-thioxoisoindolin-1-one (3a) Yellow oil, yield 68%. 1H NMR (400 MHz, DMSO-d 6): δ = 7.91–7.85 (m, 1 H), 7.84–7.80 (m, 2 H), 7.80–7.76 (m, 1 H), 5.05 (p, J = 6.9 Hz, 1 H), 1.48 (d, J = 7.0 Hz, 6 H) ppm. 13C NMR (100 MHz, DMSO-d 6): δ = 197.34, 169.70, 136.76, 135.01, 134.39, 127.45, 124.33, 123.02, 46.49, 19.86 ppm. Anal. Calcd for C11H11NOS: C, 64.36; H, 5.40; N, 6.82; S, 15.62. Found: C, 64.66; H, 5.21; N, 6.98; S, 15.37. MS (70 eV): m/z = 205 [M+].