Palladium-Mediated Reductive Heck Cyclization for the Formation of Tricyclic Sultams

Soumen Joardar; Santanu Chakravorty; Saktipada Das

doi:10.1055/s-0034-1379427

Synlett, Table of Contents

Synlett 2015; 26(03): 359-362
DOI: 10.1055/s-0034-1379427

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Palladium-Mediated Reductive Heck Cyclization for the Formation of Tricyclic Sultams

Soumen Joardar*

^aChembiotek, TCG Lifesciences Ltd., Kolkata-700 091, West Bengal, India Email: joardarsoumen@gmail.com

^bDepartment of Chemistry, University of Kalyani, Kalyani-741 235, West Bengal, India

,

Santanu Chakravorty

^bDepartment of Chemistry, University of Kalyani, Kalyani-741 235, West Bengal, India

,

Saktipada Das*

^bDepartment of Chemistry, University of Kalyani, Kalyani-741 235, West Bengal, India

› Author Affiliations

Abstract

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Abstract

Tricyclic sultams have been synthesized through sulfonation and a palladium-mediated Sonogashira cross-coupling followed by a reductive Heck cyclization. The procedure is straightforward and has been carried out under ligand-free conditions.

Key words

sultam - Heck reaction - Sonogashira cross coupling

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References

References

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31 A mixture of 2-bromo-N-(2-iodophenyl) benzenesulfonamide (2a, 1 mg, 2.29 mmol), 2-methoxyphenylacetylene (0.33 mg, 2.51 mmol), Pd (PPh₃)₂Cl₂ (32 mg, 4.5·10^–5 mmol), CuI (21 mg, 1.14·10^–4 mmol)), Et₃N (0.346 mg, 3.41 mmol), and THF (15 mL) was stirred at r.t. for 2 h. After completion of the reaction, the reaction mixture was filtered through Celite^®. H₂O (20 mL) was added to the filtrate, and the mixture was extracted with EtOAc (3 × 15 mL). The combined EtOAc extracts were washed with H₂O (3 × 15 mL), dried (Na₂SO₄), and filtered. The solvent was removed, and the residue was purified by column chromatography over silica gel using PE–EtOAc (5:1) as eluent to afford the compound 3a as a yellow solid; mp 125–128 °C; yield: 763 mg (75%). IR (film): 3088, 1609 cm^–1. ¹HNMR (400 MHz, CDCl₃): δ = 3.42 (s, 3 H), 6.72 (s, 1 H), 6.80 (d, 1 H, J = 8.3 Hz), 6.90 (t, 1 H, J = 7.44 Hz), 7.22–7.39 (m, 6 H), 7.50–7.54 (m, 1 H), 7.63–7.65 (m, 1 H), 7.78–7.83 (m, 2 H). ¹³CNMR (100 MHz, CDCl₃): δ = 60.7, 115.7, 117.1, 117.2, 121.3, 121.4, 125.4, 126.3, 126.7, 127.0, 128.9, 130.0, 132.8, 134.9, 136.4, 136.9, 138.6, 139.5, 140.7, 142.9, 143.9, 144.9, 164.0. LC–MS: m/z = 442 [M⁺ + H], 444 [M⁺ + H + 2]. Anal. Calcd for C₂₁H₁₆BrNO₃S: C, 57.02; H, 3.65; N, 3.17. Found: C, 56.94; H, 3.79; N, 3.36.
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