A Simple and Efficient Microwave-Assisted Synthesis of Substituted Isoindolinone Derivatives via Ligand-Free Pd-Catalyzed Domino C–C/C–N Coupling Reaction

Vikas Tyagi; Shahnawaz Khan; Prem M. S. Chauhan

doi:10.1055/s-0032-1318331

Synlett, Table of Contents

Synlett 2013; 24(5): 645-651
DOI: 10.1055/s-0032-1318331

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A Simple and Efficient Microwave-Assisted Synthesis of Substituted Isoindolinone Derivatives via Ligand-Free Pd-Catalyzed Domino C–C/C–N Coupling Reaction

Vikas Tyagi

Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow, 226 001, India Fax: +91(522)2623405 Email: premsc58@hotmail.com Email: prem_chauhan_2000@yahoo.com

,

Shahnawaz Khan

Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow, 226 001, India Fax: +91(522)2623405 Email: premsc58@hotmail.com Email: prem_chauhan_2000@yahoo.com

,

Prem M. S. Chauhan*

Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow, 226 001, India Fax: +91(522)2623405 Email: premsc58@hotmail.com Email: prem_chauhan_2000@yahoo.com

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Abstract

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Abstract

We have reported a microwave-assisted, ligand-free Pd-catalyzed domino C–C/C–N coupling reaction to construct diverse isoindolinone derivatives using amides and isocyanides as coupling partners. This strategy provides isoindolinone derivatives in moderate to good yield and high stereoselectivity. A broad range of amides has been tolerated and there is no need for extra-dry conditions in this reaction protocol, which offered highly diverse products and easy handling of the reaction.

Key words

ligand - Pd-catalyzed - isoindolinone - amides - isocyanides

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References

References and Notes

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10 Procedure for the Synthesis of 3a Amide 1a (1 mmol), isocyanide 2a (1.2mmol), Pd(OAc)₂ (10 mol%), Cs₂CO₃ (2 mmol.), and DMF (2 mL) as a solvent were added in a 10 mL reaction glass vial containing a stirring bar, the vial was sealed tightly with a Teflon cap and placed in microwave cavity for 15 min at a preselected temperature of 120 °C. After completion of the reaction as indicated by TLC, the resulting mixture was filtered through a pad of Celite, and the Celite was rinsed with EtOAc. The solvent was evaporated under reduced pressure, and the residue was purified by flash column chromatography on silica gel (eluent: hexane–EtOAc) affording the corresponding coupling product 3a in 89% yield. Solid; yield 89%, mp 136–138 °C. FTIR (KBr): 2985, 2410, 1722, 1690, 1656, 1287, 1132 cm^–1. ¹H NMR (300 MHz, CDCl₃): δ = 8.11 (d, J = 7.5 Hz, 1 H), 8.03 (d, J = 6.6 Hz, 1 H), 7.81–7.66 (m, 2 H), 7.39–7.35 (m, 2 H), 7.25–7.11 (m, 2 H), 1.51 (s, 9 H) ppm. ¹³C NMR (50 MHz, CDCl₃): δ = 166.7, 162.9, 159.7, 146.8, 133.6, 132.6, 131.4, 130.3, 130.2, 128.6, 127.4, 123.7, 115.2, 114.9, 54.0, 30.6 ppm. ESI-HRMS: m/z calcd for C₁₈H₁₇FN₂O [M + H]⁺: 297.1403; found: 297.1391.

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