Synlett 2018; 29(04): 509-512
DOI: 10.1055/s-0036-1591721
letter
© Georg Thieme Verlag Stuttgart · New York

Acetylenic Ester Promoted Tandem Ring Opening of Dienyl Thiazolidin-4-ones and Cyclizations: A Facile and Chemoselective Synthesis of Functionalized Pyridine-2-carboxylates

Bilash Kuila
a  Department of Chemical Sciences, I. K. Gujral Punjab Technical University, Kapurthala, Punjab-144603, India
,
Kapil Kumar
b  Department of Chemistry, Guru Nanak Dev University, Amritsar, Punjab 143005, India
,
Dinesh Mahajan
c  Drug Discovery Research Centre (DDRC), Translational Health Sciences and Technology Institute (THSTI), Faridabad-121001, India   Email: [email protected]
,
Prabhpreet Singh
b  Department of Chemistry, Guru Nanak Dev University, Amritsar, Punjab 143005, India
,
Gaurav Bhargava*
a  Department of Chemical Sciences, I. K. Gujral Punjab Technical University, Kapurthala, Punjab-144603, India
› Author Affiliations
The Board of Research in Nuclear Sciences (BRNS), India is thanked for the Research Grant (Project No.2013/37C/11/BRNS/198). The Department of Science and Technology (DST), India is also thanked for the Research Grant (Project No. SB/FT/CS-079/2012).
Further Information

Publication History

Received: 07 September 2017

Accepted after revision: 18 October 2017

Publication Date:
28 November 2017 (online)


Abstract

Acetylenic ester promoted ring opening of dienyl-thiazolidin-4-ones and subsequent electrocyclization affords 5-phenyl-6-aryl pyridine-2-carboxylates in good to excellent yields.

Supporting Information

 
  • References and Notes

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  • 24 General procedure for the preparation of alkyl 6-(aryl)-5-phenylpyridine-2-carboxylate (3a–h): To a solution of compound 1 (0.1 g, 0.2544 mmol, 1 equiv) in xylene (10 mL), DMAD (3 equiv) was added and the reaction mixture was heated to 170 °C for 16 h. Progress of the reaction was monitored by TLC taking 1 as the limiting reactant. After completion of reaction, the solvent was removed under reduced pressure. The crude product was purified by column chromatography, using a 20–25% mixture of ethyl acetate in hexane as eluent to obtain 3 as the pure product.
  • 25 Methyl 6-(2,5-dimethylphenyl)-5-phenylpyridine-2-carboxylate (3a): White solid; 1H NMR (300 MHz, CDCl3): δ = 1.83 (s, 3 H), 2.25 (s, 3 H), 4.00 (s, 3 H), 6.91 (d, J = 7.8 Hz, 1 H), 6.98 (dd, J = 7.8, 1.2 Hz, 1 H), 7.04 (s, 1 H), 7.10–7.15 (m, 2 H), 7.20–7.23 (m, 3 H), 7.88 (d, J = 7.8 Hz, 1 H), 8.19 (d, J = 7.8 Hz, 1 H); 13C NMR (CDCl3): δ = 19.1, 20.8, 52.9, 123.7, 127.7, 128.1, 128.9, 129.1, 129.9, 130.9, 132.6, 134.9, 138.4, 139.0, 140.1, 146.2, 158.6, 166.0; LRMS: m/z = 318.2 [M+1]; HRMS: m/z calcd for C21H20NO2 [MH+]: 318.1494; found: 318.1490.
  • 26 Ethyl 6-(2,5-dimethylphenyl)-5-phenylpyridine-2-carboxylate (3e): Yellow solid; 1H NMR (300 MHz, CDCl3): δ = 1.25 (t, J = 7.8 Hz, 3 H), 1.85 (s, 3 H), 2.22 (s, 3 H), 4.23 (q, J = 7.8 Hz, 2 H), 6.94–7.05 (m, 3 H), 7.13–7.25 (m, 5 H), 7.89 (d, J = 7.5 Hz, 1 H), 8.16 (d, J = 7.5 Hz, 1 H); 13C NMR (CDCl3): δ = 15.5, 18.9, 20.8, 60.5, 123.7, 127.8, 128.3, 128.7, 129.9, 130.4, 131.0, 132.6, 135.2, 138.4, 139.1, 139.9, 146.2, 158.4, 165.7; LRMS: m/z = 332 [M+1]; HRMS: m/z calcd for C22H22NO2 [MH+]: 332.1651; found: 332.1655.