Synlett 2012; 23(18): 2627-2630
DOI: 10.1055/s-0032-1317326
letter
© Georg Thieme Verlag Stuttgart · New York

Efficient, One-Pot, BF3·OEt2-Mediated Synthesis of Substituted N-Aryl Lactams

Devdutt Chaturvedi*
a   Laboratory of Medicinal Chemistry, Amity Institute of Pharmacy, Amity University Uttar Pradesh, Lucknow Campus, Lucknow 226010, U. P., India   Fax: +91(522)2399610   Email: devduttchaturvedi@gmail.com   Email: dchaturvedi@lko.amity.edu
,
Amit K. Chaturvedi
b   Synthetic Research Laboratory, Department of Chemistry, B. S. A. P. G. College, Mathura 281004, U. P., India
,
Nisha Mishra
b   Synthetic Research Laboratory, Department of Chemistry, B. S. A. P. G. College, Mathura 281004, U. P., India
,
Virendra Mishra
b   Synthetic Research Laboratory, Department of Chemistry, B. S. A. P. G. College, Mathura 281004, U. P., India
› Author Affiliations
Further Information

Publication History

Received: 26 June 2012

Accepted after revision: 06 September 2012

Publication Date:
18 October 2012 (online)


Abstract

A quick, efficient, one-pot, BF3·OEt2-mediated synthesis of substituted N-aryl lactams in good to excellent yields by reaction of various substituted arenes with a variety of ω-azido alkanoic acid chlorides at room temperature is reported.

 
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  • 28 Typical Experimental Procedure for the Synthesis of Substituted N-Aryl Lactams An equimolar amount of substituted arene and the corresponding ω-azido alkanoic acid chloride were taken in anhyd CH2Cl2 (25 mL) and stirred for 10 min at r.t. To this mixture, BF3·OEt2 (0.1 mol, with respect to arene) was added slowly in 2–3 small portions at r.t. The reaction was continued until completion (cf. Table 1) as confirmed by TLC. The reaction mixture was then poured into distilled H2O (50 mL) and extracted with CH2Cl2. The organic layer was separated and dried over anhyd Na2SO4 and then concentrated to afford the desired substituted N-aryl lactam compound. Data of Selected Compounds 1-(3,4-Dimethoxyphenyl)piperidin-2-one (3aa) Colorless oil. 1H NMR (300MHz, CDCl3): δ = 1.92–1.95 (m, 4 H), 2.55 (t, J = 6.2 Hz, 2 H), 3.61 (t, J = 5.5 Hz, 2 H), 3.86 (s, 3 H), 3.87 (s, 3 H), 6.77–6.78 (m, 2 H), 6.86–6.88 (m, 1 H). 13C NMR (75 MHz, CDCl3): δ = 21.3, 23.4, 32.7, 52.0, 55.7, 55.8, 110.0, 111.2, 118.0, 136.4, 147.6, 149.0, 170.0. MS (EI): m/z (%) = 235 (100) [M+], 220, 166. HRMS (EI): m/z calcd for C13H17O3N [M+]: 235.1208; found: 235.1208. 1-(3,5-Dimethoxyphenyl)pyrrolidin-2-one (3ba) White solid; mp 85–86 °C. IR (CH2Cl2): ν = 1069, 1154, 1208, 1249, 1275, 1324, 1347, 1393, 1478, 1598, 1697, 2841, 2958 cm–1. 1H NMR (300 MHz, CDCl3, TMS): δ = 2.14 (tt, J = 8.4 Hz, 6.6 Hz, 2 H, CH2), 2.61 (t, J = 8.4 Hz, 2 H, CH2), 3.80 (s, 6 H, OCH3), 3.83 (t, J = 6.6 Hz, 2 H, CH2), 6.27 (t, J = 2.4 Hz, 1 H, Ar), 6.86 (d, J = 2.4 Hz, 2 H, Ar). 13C NMR (75 MHz, CDCl3, TMS): δ = 17.8, 32.9, 48.9, 55.3, 96.4, 98.3, 141.1, 160.7, 174.3. MS (EI): m/z (%) = 221 (100) [M+], 192 (23), 178 (9), 166 (75), 162(7), 151 (5), 136 (12), 122(6), 108(5). Anal. Calcd (%) for C12H15NO3: C, 65.14; H, 6.83; N, 6.33. Found: C, 64.99; H, 6.85; N, 6.25.