A Practical Synthesis of 4-Azaindole

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Abstract:

An improved method for practical synthesis of 4-azaindole from 2-chloro-3-nitropyridine has been developed. In the key step, decarboxylation with acetic acid afforded 3-nitro-2-pyridylacetonitrile in high yield.

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353-356

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December 2013

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© 2014 Trans Tech Publications Ltd. All Rights Reserved

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[1] E. Sanders-Bush, S.E. Mayer, in: Goodman & Gilman's The Pharmacological Basis of Therapeutics, edtied by McGraw-Hill: New York, (1996), p.249.

Google Scholar

[2] J. Rodriguez, Feraud, M. Spec. Chem. Mag. Vol. 25 (2005), p.16.

Google Scholar

[3] D. Fernandez, A. Ahaidar, G. Danelon, P. Cironi, M. Marfil, O. Perez, C. Cuevas, F. Albericio, J.A. Joule, M. Alvarez, Monatsh. Chem. Vol. 135 (2004), p.615.

DOI: 10.1002/chin.200438236

Google Scholar

[4] P.M. Fresneda, S. Delgado, A. Francesch, I. Manzanares, C. Cuevas, P. Molina, J. Med. Chem. Vol. 49 (2006) p.1217.

Google Scholar

[5] P. Beswick, R. Gleave,; M. Swarbrick, Patent WO 0169241, (2005).

Google Scholar

[6] P.C. Tang, L. Sun, G. McMahon, U.S. Patent 6849641, (2005).

Google Scholar

[7] L. David, P. Hansen, Patent WO 099205, (2004).

Google Scholar

[8] T. Wang, O.B. Wallace, Z. Zhang, N.A. Meanwell, J.A. Bender, Patent WO 0622551, (2001).

Google Scholar

[9] S. Benoit, S. Gingras, N. Soundararajan, Patent WO 0822891, (2003).

Google Scholar

[10] F. Pin, F. Buron, F. Saab, L. Colliandre, S. Bourg, F. Schoentgen, R.L. Guevel, C. Guillouzo, S. Routier, Med. Chem. Commun. Vol. 2 (2011), p.899.

DOI: 10.1039/c1md00141h

Google Scholar

[11] O. Kruber, Chem. Ber. Vol. 128 (1943), p.128.

Google Scholar

[12] D. Hands, B. Bishop, M. Cameron, J.S. Edwards, I.F. Conttrell, S.H.B.A. Wright, Synthesis (1996) p.877.

Google Scholar

[13] L.N. Yakhontov, V.A. Azimov, E.I. Lapan, Tetrahedron Lett (1969), p. (1909).

Google Scholar

[14] M.H. Fisher, A.R.J. Matzuk, Heterocycl. Chem. Vol. 6 (1969), p.775.

Google Scholar

[15] R.H. Dodd, X. Doisy, P. Potier, Heterocycles Vol. 28 (1989), p.1101.

Google Scholar

[16] N.R. Curtis, J.J. Kulagowski, P.D. Leeson, M.P. Ridgill, F. Emms, S.B. Freedman, S. Patel, S. Patel, Biorg. Med. Chem. Lett. Vol. 9 (1999), p.585.

DOI: 10.1016/s0960-894x(99)00025-6

Google Scholar

[17] A.R. Battersby, E. McDonald, H.K.W. Wurziger, K.J.J. James, Chem. Soc. Chem. Commun. (1975), p.493.

Google Scholar

[18] I. Mahadevan, M.J. Rasmussen, Heterocycl. Chem. Vol. 29 (1992) p.359.

Google Scholar

[19] R.R. Lorenz, B.F. Tullar, C.F. Koelsch, S. Archer, J. Org. Chem. Vol. 30 (1965) p.2531.

Google Scholar

[20] S.S. Park, J. -K. Choi, E.K. Yum, D. -C. Ha, Tetrahedron Lett. Vol. 39 (1998), p.627.

Google Scholar

[21] L. Xu, I.R. Lewis, S.K. Davidsen, J.B. Summers, Tetrahedron Lett. Vol. 39 (1998), p.5159.

Google Scholar

[22] F. Ujjainwalla, D. Warner, Tetrahedron Lett. Vol. 39 (1998), p.5355.

Google Scholar

[23] R.B. Katz, M. Voyle, Synthesis (1989), p.314.

Google Scholar

[24] T. Sakamoto, Y. Kondo, S. Iwashita, H. Yamanaka, Chem. Pharm. Bull. Vol. 35 (1987), p.1823.

Google Scholar