Synlett 2016; 27(03): 404-408
DOI: 10.1055/s-0035-1560825
letter
© Georg Thieme Verlag Stuttgart · New York

Microwave-Assisted Nickel-Catalyzed One-Pot Synthesis of 2,4,5-Trisubstituted Imidazoles

Tejpal Singh Chundawat
a   Organic Synthesis Research Laboratory, Department of Chemistry, A.R.S.D. College, University of Delhi, New Delhi-110021, India   Email: sunitabhagat28@gmail.com   Email: chundawatchem@yahoo.co.in
b   Department of Applied Sciences, The Northcap University (formerly ITM University), Gurgaon-122017, Haryana, India
,
Nutan Sharma
a   Organic Synthesis Research Laboratory, Department of Chemistry, A.R.S.D. College, University of Delhi, New Delhi-110021, India   Email: sunitabhagat28@gmail.com   Email: chundawatchem@yahoo.co.in
,
Poonam Kumari
a   Organic Synthesis Research Laboratory, Department of Chemistry, A.R.S.D. College, University of Delhi, New Delhi-110021, India   Email: sunitabhagat28@gmail.com   Email: chundawatchem@yahoo.co.in
,
Sunita Bhagat*
a   Organic Synthesis Research Laboratory, Department of Chemistry, A.R.S.D. College, University of Delhi, New Delhi-110021, India   Email: sunitabhagat28@gmail.com   Email: chundawatchem@yahoo.co.in
› Author Affiliations
Further Information

Publication History

Received: 27 July 2015

Accepted after revision: 04 October 2015

Publication Date:
30 November 2015 (online)


Abstract

A novel, highly efficient, and one-pot microwave-assisted synthesis of 2,4,5-trisubstituted imidazoles using a newly developed Schiff’s base complex nickel catalyst (Ni-C) is described. The approach involves the reaction of various aldehydes with benzil and ammonium acetate in the presence of the Ni-C catalyst to furnish cyclized products in excellent yields. The Ni-C catalyst exhibited remarkable catalytic activity with respect to the reaction time in the microwave reactor. The catalyst could be easily recovered by simple filtration and reused.

Supporting Information

 
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  • 38 General Procedure for the Synthesis of Substituted 2,4,5-Triphenylimidazoles A mixture of benzil (1, 2.3 mmol), benzaldehyde (2, 2.3 mmol), NH4OAc (3, 2.8 mmol), and the catalytic amount of Ni-C (10 mol%) in EtOH (2 mL) were taken in a microwave tube (10 mL) and exposed to microwave irradiation for 15–30 min. The completion of reaction was monitored by TLC. After completion of reaction, EtOAc was added to the reaction mixture, and the catalyst was recovered by filtration. After that organic layer was washed with H2O, dried over Na2SO4, and concentrated under reduced pressure. The obtained residues were purified by column chromatography using silica gel (100–200 mesh size) in 20% EtOAc–hexane as eluent to provide the desired compound 4. Representative Spectroscopic Data Compound 4g: 1H NMR (400 MHz, DMSO): δ = 12.98 (s, 1 H), 8.29–8.27 (d, J = 8.79 Hz, 2 H), 7.85–7.83 (d, J = 8.05 Hz, 2 H), 7.55–7.36 (m, 7 H), 7.32–7.30 (t, J = 7.32 Hz, 2 H), 7.23–7.21 (t, J = 7.32 Hz, 1 H). 13C NMR (100 MHz, DMSO): δ = 144.01, 137.76, 134.84, 133.99, 130.76, 129.25, 128.76, 127.93, 127.14, 126.78, 125.80, 125.60, 123.00. IR (KBr): ν = 3432, 3025, 1621, 1325, 1131, 1064, 697 cm–1. ESI-MS: m/z = 365.54 [M + 1]. Anal. Calcd for C22H15F3N2: C, 72.52, H, 4.15; N, 7.69. Found: C, 72.31; H, 3.94; N, 7.64. Compound 4i: 1H NMR (400 MHz, DMSO): δ = 12.63 (s, 1 H), 7.97–7.94 (dd, 1 H), 7.74–7.71 (dd, 1 H), 7.49–7.38 (m, 7 H), 7.28–7.26 (t, J = 7.32 Hz, 2 H), 7.19–7.17 (t, J = 7.32 Hz, 2 H). 13C NMR (100 MHz, DMSO): δ = 155.47, 152.99, 150.29, 139.13, 137.43, 134.71, 130.50, 128.66, 127.14, 126.74, 116.99, 115.65, 107.31. IR (KBr): ν = 3442, 3068, 1614, 1604, 1490, 1185, 1061, 696 cm–1. ESI-MS: m/z = 351.29 [M + 1]. Anal. Calcd for C21H13F3N2: C, 71.99; H, 3.74; N, 8.00. Found: C, 71.63; H, 3.78; N, 7.71. Compound 4r: 1H NMR (400 MHz, DMSO): δ = 12.89 (s, 1 H), 7.76–7.74 (d, J = 6.59 Hz, 2 H), 7.54–7.38 (m, 8 H), 7.32–7.28 (t, J = 7.32 Hz, 2 H), 7.24–7.21 (m, 1 H). 13C NMR (100 MHz, DMSO): δ = 163.95, 161.65, 143.23, 137.58, 134.70, 133.50, 130.65, 128.78, 127.15, 108.12, 103.42. IR (KBr): ν = 3425, 3076, 1626, 1467, 1213, 1074, 693 cm–1. ESI-MS: m/z = 333.14 [M + 1]. Anal. Calcd for C21H14F2N2: C, 75.89; H, 4.25; N, 8.43. Found: C, 75.61; H, 3.89; N, 8.20.
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