A general synthesis of 1-(dialkylaminomethyl)indoles

Synlett

Volumn , Issue 10, 1998, Pages 1123-1125

  Love, Brian E ^a   Nguyen, Binh T ^a  

^a EAST CAROLINA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 23944443610     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1883     Document Type: Article

References (29)

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4. (b) Katritzky, A. R.; Rewcastle, G. W.; Fan, W. Q. J. Org. Chem. 1988, 53, 5685.
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6. (a) Katritzky, A. R.; Pilarski, B.; Urogdi, L. Org. Prep. Proced. Int. 1989, 27, 135.
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9. (a) Katritzky, A. R.; Rachwal, S.; Hitchings, G. J. Tetrahedron 1991, 47, 2683.
10. (b) Katritzky, A. R.; Lan, X.; Fan, W.-Q. Synthesis 1994, 445.
11. 1-(Dialkylaminomethyl)benzotriazoles (2) are typically contaminated with small amounts of the corresponding 2-(dialkylaminomethyl)benzotriazoles. As these isomeric compounds display essentially the same reactivity, the presence of both isomers is not detrimental to the success of the reaction. For a discussion of this isomerism, see: Katritzky, A. R.; Yannakopoulou, K.; Kuzmierkiewicz, W.; Aurrecoechea, J. M.; Palenik, G. J.; Koziol, A. E.; Szczesniak, M. J. Chem. Soc. Perkin Trans. 1 1987, 2673,
12. Katritzky, A. R.; Yannakopoulou, K. Heterocycles 1989, 28, 1121, and reference 18.
13. (a) Katritzky, A. R.; Yannakopoulou, K.; Lue, P.; Rasala, D.; Urogdi, L. J. Chem. Soc. Perkin Trans. 1 1989, 225;
14. (b) Katritzky, A. R.; Strah, S.; Belyakov, S. A. Tetrahedron 1998, 54, 7167.
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20. Percentages for compounds 2c, f & g may be slightly inaccurate due to partial overlap of the methylene signal of 3 with a small signal from residual THF.
21. 3): δ 137.8, 136.4, 128.6, 128.5, 128.4, 127.6, 125.5, 121.6, 120.9, 119.7, 109.8, 102.5, 78.8, 66.8, 50.6.
22. Love, B. E.; Raje, P. S. Heterocycles 1993, 55, 1259.
23. 3) for products 2 are as follows: 2a: 7.64 (d, J = 7.9 Hz, 1H), 7.56 (d, J = 8 Hz, 1H), 7.5-7.1 (m, 3H), 6.50 (d, J = 3.2 Hz, 1H), 4.67 (s, 2H), 2.25 (s, 6H); 2b: 7.64 (d, J = 7.6 Hz, 1H), 7.46 (d, J = 7 Hz, 1H), 7.4-7.0 (m, 3H), 6.52 (d, J = 2.5 Hz, 1H), 4.93 (s, 2H), 2.8-2.5 (m, 4H), 1.9-1.6 (m, 4H); 2c: 7.63 (d, J = 7 Hz, 1H), 7.46 (d, J = 7 Hz, 1H), 7.4-7.0 (m, 3H), 6.50 (d, J = 3.2 Hz, 1H), 4.81 (s, 2H), 2.7-2.4 (m, 4H), 1.7-1.5 (m, 4H), 1.5-1.2 (m, 2H); 2d: 7.62 (d, J = 8 Hz, 1H), 7.47 (d, J = 8 Hz, 1H), 7.3-7.0 (m, 3H), 6.53 (d, J = 3.2 Hz, 1H), 4.78 (s, 2H), 3.8-3.6 (m, 4H), 2.6-2.4(m, 4H); 2e: 7.60 (d, J = 8 Hz, 1H), 7.45 (d, J = 8 Hz, 1H), 7.3-7.0 (m, 3H), 6.48 (d, J = 3 Hz, 1H), 4.82 (s, 2H), 2.7-2.5 (m, 1H), 2.24 (s, 3H), 1.9-1.5 (m, 5H), 1.4-1.0 (m, 5H); 2f: 7.60 (d, J = 8 Hz, 1H), 7.45 (d, J = 8 Hz, 1H), 7.3-7.0 (m, 3H), 6.49 (d, J = 3.2 Hz, 1H), 4.86 (s, 2H), 2.6-2.4 (m, 4H), 1.6-1.2 (m, 8H), 0.87 (t, J = 7.3 Hz, 6H); 2g: 7.62 (d, J = 8.0 Hz, 1H), 7.40 (d, J = 7.9 Hz, 1H), 7.3-7.0 (m, 3H), 6.48 (d, J = 3.1 Hz, 1H), 4.64 (s, 2H), 2.7-2.3 (m, 8H), 2.21 (s, 3H).
24. (1a,c,d): Katritzky, A. R.; Belyakov, S. A.; Durst, H. D.; Xu, R.; Dalal, N. S. Can. J. Chem. 1994, 72, 1849.
25. (1e): Lindsay Smith, J. R.; Sadd, J. S. J. Chem. Soc. Perkin Trans. 1 1975, 1181.
26. (1f): Katritzky, A. R.; Shobana, N.; Harris, P. A. Tetrahedron Lett. 1991, 32, 4247.
27. (1g): Collino, F.; Volpe, S. Boll. Chim. Farm. 1982, 121, 167
28. (Chem. Abstr. 1982, 97, 162889b).
29. Aldrich Chemical Co., Milwaukee, WI.