A stereoselective route to polysubstituted tetrahydroquinolines by benzotriazole-promoted condensation of aliphatic aldehydes and aromatic amines

Journal of Organic Chemistry

Volumn 65, Issue 10, 2000, Pages 3148-3153

  Talukdar, Sanjay ^a,b   Chen, Chao Tsen ^a   Fang, Jim Min ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^b BHABHA ATOMIC RESEARCH CENTRE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AROMATIC AMINE; BENZOTRIAZOLE DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; MOLECULAR INTERACTION; POLYMERIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034685750     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000033x     Document Type: Article

References (30)

1. For review of the chemistry of benzotriazole, see: (a) Katritzky, A. R.; Rachwal, S.; Hitchings, G. J. Tetrahedron 1991, 47, 2683.
2. (b) Katritzky, A. R.; Belyakov, S. A. Aldrichim. Acta 1998, 31, 35.
3. (c) Katritzky, A. R.; Lan, X.; Yang, J. Z.; Denisko, O. V. Chem. Rev. 1998, 98, 409.
4. Katritzky, A. R.; Racheal, B.; Rachwal, S. J. Chem. Soc., Perkin Trans, 1 1987, 805.
5. Katritzky, A. R.; Long, Q.-H.; Lue, P.; Jozwiak, A. Tetrahedron 1990, 45, 8153.
6. Katritzky, A. R.; Rachwal, B.; Rachwal, S. J. Org. Chem. 1995, 60, 2588.
7. (a) Leeson, P. D.; Carling, R. W.; Moore, K. W.; Moseley, A. M.; Smith, J. D.; Stevenson, G.; Chan, T.; Baker, R.; Foster, A. C.; Grimwood, S.; Kemp, J. A.; Marshall, G. R.; Hoogsteen, K. J. Med. Chem. 1992, 35, 1954.
8. (b) Katritzky, A. R.; Rachwal, S.; Rachwal, B. Tetrahedron 1996, 52, 15031.
9. For reviews of imino Diels-Alder reactions, see: (a) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic: San Diego, 1987; Chapters 2 and 9.
10. (b) Weinreb, S. M. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, 401-449.
11. (c) Kobayashi, S. In Transition Metals for Organic Synthesis - Building Blocks and Fine Chemicals; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 1998; Vol. 1, 285-312.
12. For representative examples of imino Diels-Alder reactions, see: (a) Narasaka, K.; Shibata, T. Heterocycles 1993, 35, 1039.
13. (b) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423.
14. (c) Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 7357.
15. (d) Annunziata, R.; Cinquini, M.; Cozzi, F.; Molteni, V.; Schupp, O. Tetrahedron 1997, 53, 9715.
16. (e) Babu, G.; Perumal, P. T. Tetrahedron Lett. 1998, 39, 3225.
17. (f) Hadden, M.; Stevenson, P. J. Tetrahedron Lett. 1999, 40, 1215.
18. (g) Batey, R. A.; Simoncic, P. D.; Lin, D.; Smyj. P.; Lough, A. J. Chem. Commun. 1999, 651.
19. (h) Ma, Y.; Qian, C.; Xie, M.; Sun. J. J. Org. Chem. 1999, 64, 6462.
20. Katritzky, A. R.; Nichols, D. A.; Qi, M.; Yang, B. J. Heterocycl. Chem. 1997, 34, 1259.
21. Jencks, W. P. Prog. Phys. Org. Chem. 1964, 2, 63.
22. For acid-catalyzed [4 + 2] cycloadditions between enamines and (benzylidene)anilines, see: Nomura, Y.; Kimura, M.; Takeuchi, Y.; Tomoda, S. Chem. Lett. 1978, 267. For a condensation between N-methylaniline and hydroxyacetaldehyde, see: Turner, A. B.; McBain, B. I.; Howie, R. A. J. Chem. Soc., Perkin Trans. 1 1986, 1151. The reaction has been conducted in EtOH at 20°C for 48 h to give a single 2,3-cis-2,4-trans isomer of 3-hydroxy-2-hydroxymethyl-1-methyl-4-(N- methylanilino)-1,2,3,4-tetrahydroquinoline in 45% yield. The stereochemistry is different from that of THQ 9f with the 2,3-trans-2,4-cis configuration obtained by condensation of N-methylaniline and phenylacetaldehyde (our present investigation).
23. For acid-catalyzed [4 + 2] cycloadditions between enamines and (benzylidene)anilines, see: Nomura, Y.; Kimura, M.; Takeuchi, Y.; Tomoda, S. Chem. Lett. 1978, 267. For a condensation between N-methylaniline and hydroxyacetaldehyde, see: Turner, A. B.; McBain, B. I.; Howie, R. A. J. Chem. Soc., Perkin Trans. 1 1986, 1151. The reaction has been conducted in EtOH at 20°C for 48 h to give a single 2,3-cis-2,4-trans isomer of 3-hydroxy-2-hydroxymethyl-1-methyl-4-(N-methylanilino)-1,2,3,4- tetrahydroquinoline in 45% yield. The stereochemistry is different from that of THQ 9f with the 2,3-trans-2,4-cis configuration obtained by condensation of N-methylaniline and phenylacetaldehyde (our present investigation).
24. 2.
25. Funabashi, M.; Yoshimura, J. Bull. Chem. Soc. Jpn. 1968, 41, 2735. Dimerization of N-phenyl (R)-glyceraldimine acetonide by the catalysis of acetic acid gives the THQ 9j (30%) as a mixture of two isomers. This paper reported only one example, and the protocol was not generalized.
26. Lu, L.; Chang, H.-Y.; Fang, J.-M. J. Org. Chem. 1999, 64, 843.
27. Both the divalent and trivalent samarium species can act as hard Lewis acids to coordinate with hard Lewis bases such as oxygen and nitrogen atoms. See: Gu, X.; Curran, D. P. In Transition Metals for Organic Synthesis - Building Blocks and Fine Chemicals; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 1998; Vol. 1, pp 425-438.
28. 4, containing a molecule of EtOAc) were obtained, respectively, via slow evaporation of the solutions of 9j and 9n in EtOAc-hexane, in closed chambers saturated with hexane.
29. 2 has been reported to reduce the N-(N′,N′-dialkylaminoalkyl)benzotriazoles derived from nonenolizable aldehydes to generate the amino α-radical intermediates, which undergo a coupling reaction to give the corresponding 1,2-diamines.
30. Hartman, G. D.; Phillips, B. T.; Halczenko, W. J. Org. Chem. 1985, 50, 2423.