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

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.

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

References and Notes

1 Bhargava G. Kumar V. Mahajan MP. Tetrahedron Lett.  2007,  48:  2365 

For leading references, see:

2a Daly JW. Spande TF. Alkaloids: Chemical and Biological Perspectives   Vol. 4:  Pelletier SW. Wiley; New York: 1986.  p.1-254  

2b Fodor GB. Colasanti B. Alkaloids: Chemical and Biological Perspectives   Vol. 3:  Pelletier SW. Wiley; New York: 1985.  p.1-91  

2c Boger D. Weinreb SM. Hetero Diels-Alder Methodology in Organic Synthesis   Academic; San Diego: 1987.  Chap. 2. p.34-70  

2d Boger D. Weinreb SM. Hetero Diels-Alder Methodology in Organic Synthesis   Academic; San Diego: 1987.  Chap 9. p.239-299  ; and references therein

2e Boger DL. Patel M. In Progress in Heterocyclic Chemistry   Suschitzky H. Scriven EFV. Pergamon; New York: 1989.  p.1-30  

2f Kametani T. Hibino S. Adv. Heterocycl. Chem.  1987,  42:  246 

3a Tietze LF. Kettschau G. Top. Curr. Chem.  1997,  189:  1 

3b Kobayashi S. Eur. J. Org. Chem.  1999,  15 

3c Panunzio M. Zarantonello P. Org. Process Res. Dev.  1988,  2:  49 

3d Enders D. Meyer O. Liebigs Ann.  1996,  1023 

3e Waldmann H. In Organic Synthesis Highlights II   Waldman H. VCH; New York: 1995.  p.37-47  

3f Waldmann H. Synthesis  1994,  535 

3g Waldmann H. Braun M. Gazz. Chim. Ital.  1991,  121:  277 

3h Waldmann H. Synlett  1995,  133 

3i Barluenga J. Joglar J. Gonzalez FJ. Fustero S. Synlett  1990,  129 

3j Parker DT. In Organic Synthesis in Water   Grieco PA. Blacky Academic and Professional; London: 1998. 

3k Barluenga J. Tomas M. Adv. Heterocycl. Chem.  1993,  57:  1 

For selected examples, see:

4a Hermitage S. Howard JAK. Jay D. Pritchard RG. Probert MR. Whiting A. Org. Biomol. Chem.  2004,  2:  2451 

4b Badorrey R. Cativiela C. Dfaz-de-Villegas MD. Galvez JA. Tetrahedron  1999,  55:  7601 

5 Garcia A.-B. Valdes C. Cabal M.-P. Tetrahedron Lett.  2004,  45:  4357 

For recent reviews, see:

6a Buonora P. Olsen J.-C. Oh T. Tetrahedron  2001,  57:  6099 

6b Jørgensen KA. Angew. Chem. Int. Ed.  2000,  39:  3558 ; and references cited therein

6c Orr RK. Calter MA. Tetrahedron  2003,  59:  3545 ; and references cited therein

7a Kobayashi S. Nagayama S. J. Am. Chem. Soc.  1996,  118:  8977 

7b Kobayashi S. Ishitani H. Nagayama S. Chem Lett.  1995,  24:  423 

7c Kobayashi S. Ishitani H. Nagayama S. Chem. Lett.  1995,  24:  423 

7d Ishitani H. Kobayashi S. Tetrahedron Lett.  1996,  37:  7357 

7e Kobayashi S. Araki M. Ishitani H. Nagayama S. Hachiya I. Synlett  1995,  233 

7f Kobayashi S. Ishitani H. Nagayama S. Synthesis  1995,  1195 

8 Sharma AK. Mazumdar SN. Mahajan MP. J. Org. Chem.  1996,  61:  5506 

9a Goel RK. Kumar V. Mahajan MP. Bioorg. Med. Chem. Lett.  2005,  15:  2145 

9b Bedi PMS. Kumar V. Mahajan MP. Bioorg. Med. Chem. Lett.  2004,  14:  5211 

9c Goel RK. Thind JS. Bal CS. Mahajan MP. Kulkarni SK. Pharmazie  2005,  60:  369 

9d Bhargava G. Mahajan MP. Saito T. Otani T. Kurashima M. Sakai K. Eur. J. Org. Chem.  2005,  2397 

For reviews on this subject, see:

10a Southgate R. Contemp. Org. Synth.  1994,  1:  417 

10b Southgate R. Branch C. Coulton S. Hunt E. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products   Vol. 2:  Lukacs G. Springer; Berlin: 1993.  p.621 

10c Ojima I. The Organic Chemistry of β-Lactams   Georg GI. VCH; New York: 1993.  p.197 

10d The Chemistry of β-Lactams   Page MI. Chapman and Hall; London: 1992. 

10e Southgate R. Elson S. In Progress in the Chemistry of Organic Natural Products   Vol. 47:  Herz W. Grisebach H. Kirby GW. Tamm C. Springer; Vienna: 1985.  p.1 

For reviews, see:

11a Mascaretti OA. Boschetti CE. Danelon GO. Mata EG. Roveri OA. Curr. Med. Chem.  1995,  1:  441 

11b Edwards PD. Bernstein PR. Med. Res. Rev.  1994,  14:  127 

12a Vaccaro WD. Davis HR. Bioorg. Med. Chem. Lett.  1998,  8:  313 

12b Vaccaro WD. Sher R. Davis HR. Bioorg. Med. Chem. Lett.  1998,  8:  35 

12c Burnett DA. Tetrahedron Lett.  1994,  35:  7339 

13a Borthwick AD. Weingarten G. Haley TM. Tomaszewski M. Wang W. Hu Z. Bedard J. Jin H. Yuen L. Mansour TS. Bioorg. Med. Chem. Lett.  1998,  8:  365 

13b Ogilvie W. Bailey M. Poupart M.-A. Abraham A. Bhavsar P. Bonneau P. Bordeleau J. Bousquet Y. Chabot C. Duceppe J.-S. Fazal G. Goulet S. Grand-Maitre C. Guse I. Halmos T. Lavallee P. Leach M. Malefant E. O’Meara J. Plante R. Plouffe C. Poirier M. Soucy F. Yoakim C. Deziel R. J. Med. Chem.  1997,  40:  4113 

14 Han WT. Trehan AK. Wright JJK. Federici ME. Seiler SM. Meanwell NA. Bioorg. Med. Chem.  1995,  3:  1123 

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.