Regio- and Chemoselective Unprecedented Imino-Diels-Alder Reactions of 1-Substituted Unactivated Dienes with N-Aryl Imines - Part II

Gaurav Bhargava; Mohinder P. Mahajan; Takao Saito

doi:10.1055/s-2008-1072507

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Synlett 2008(7): 983-986
DOI: 10.1055/s-2008-1072507

LETTER

Regio- and Chemoselective Unprecedented Imino-Diels-Alder Reactions of 1-Substituted Unactivated Dienes with N-Aryl Imines - Part II [1]

Gaurav Bhargava^a, Mohinder P. Mahajan*^a, Takao Saito^b
^a Department of Applied Chemistry, Guru Nanak Dev University, Amritsar 143005, Punjab, India
Fax: +91(183)225881920; e-Mail: mahajanmohinderp@yahoo.co.in;
^b Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan

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Publication History

Received 31 October 2007
Publication Date:
17 March 2008 (online)

Abstract
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Abstract

The chemo- as well as regioselective participation of N-aryl imines as 4π component in aza-Diels-Alder reactions with 3-butadienyl-2-azetidinones in the presence of Lewis acid catalysts resulting in novel quinoline derivatives is described.

Key words

dienyl-2-Azetidinones - imino-Diels-Alder reactions - Lewis acid - regioselectivity - chemoselectivity - quinoline derivatives

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15

3-[2-(6-Methoxy-2-phenyl-quinolin-4-yl)-vinyl]-1,4-diphenyl-azetidin-2-one (4a): white solid, mp 170-171 °C. ¹H NMR (600 MHz, CDCl₃): δ = 3.90 (s, 3 H, OCH₃), 4.12 (dd, J = 2.3, 7.6 Hz, 1 H, H₃), 4.90 (d, J = 2.3 Hz, 1 H, H₄), 6.71 (dd, J = 7.6, 15.5 Hz, 1 H, H₅), 7.10 (t, J = 6.8 Hz, 1 H, arom.), 7.41 (m, 13 H, arom. and H₁₂), 7.50 (d, J = 15.5 Hz, 1 H, H₆), 7.52 (s, 1 H, H₁₄), 7.90 (s 1 H, H₈), 8.08 (d, J = 9.2 Hz, 1 H, H₁₁) 8.13 (d, J = 7.4 Hz, 2 H, H₁₈). ¹³C NMR (75 MHz, CDCl₃): δ = 53.4, 61.6, 63.8, 101.4, 115.9, 117.1, 122.0, 124.2, 125.9, 127.2, 128.0, 128.5, 128.7, 128.8, 128.9, 129.1, 129.3, 130.3, 131.7, 137.0, 137.4, 139.7, 141.2, 144.7, 154.8, 157.8, 164.7. MS: m/z = 482 [M]⁺. IR (KBr): ν_max = 1752, 1627, 1565, 1508, 1387 cm^-1. Anal. Calcd for C₃₃H₂₆N₂O₂: C, 82.13; H, 5.43; N, 5.81. Found: C, 82.27; H, 5.58; N, 5.66.