Synthesis of Novel N-Aryl-1H-indazolamines from Amino-1H-indazoles and Arylboronic Acids

Udutha Kumara Swamy; H. Rama Mohan; U. Viplava Prasad

doi:10.14233/ajchem.2014.16794

Issue

Vol. 26 No. 22 (2014): Vol 26 Issue 22

Issue Published : November 6, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis of Novel N-Aryl-1H-indazolamines from Amino-1H-indazoles and Arylboronic Acids

https://doi.org/10.14233/ajchem.2014.16794

Udutha Kumara Swamy

Laurus Labs Private Limited, IKP Knowledge Park, Turkapally, Shameerpet, Hyderabad-500 078, India

H. Rama Mohan

Advinus Therapeutics Limited, Peenya Industrial Area, Bangalore-560 058, India

U. Viplava Prasad

Department of Organic Chemistry, Foods, Drugs and Water, Andhra University, Visakhapatnam-530 003, India

Corresponding Author(s) : Udutha Kumara Swamy

kumarudutha@gmail.com

Asian Journal of Chemistry, Vol. 26 No. 22 (2014): Vol 26 Issue 22
Article Published : November 6, 2014

Abstract

An efficient and high-yielding synthesis of N-aryl-1H-indazolamines from amino-1H-indazole and arylboronic acids are described. In this study a series of novel N-aryl-1H-indazolamines (1a-i) were synthesized using arylboronic acids and amino-1H-indazoles (3a-c).

Keywords

Amino-1H-indazole Arylboronic acid

Kumara Swamy, U., Rama Mohan, H., & Viplava Prasad, U. (2014). Synthesis of Novel N-Aryl-1H-indazolamines from Amino-1H-indazoles and Arylboronic Acids. Asian Journal of Chemistry, 26(22), 7539–7543. https://doi.org/10.14233/ajchem.2014.16794

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References

(a) J. Elguero, in eds.: A.R. Katritzky and C.W. Rees, Comprehensive Heterocyclic Chemistry, Pyrazoles and their Benzo Derivatives, Pergamon Press: Oxford, Vol. 5, pp. 167-303 (1984); (b) J. Elguero, in eds.: A.R. Katritzky, C.W. Rees and E.F.V. Scriven, Comprehensive Heterocyclic Chemistry II: Pyrazoles, Pergamon Press: Oxford, Vol. 3, pp. 1-75 (1996).
(a) W. Stadlbauer, in ed.: E. Schaumann, In Houben-Weyl, Methoden der Organischen Chemie: Indazole (Benzopyrazole); Georg-Thieme-Verlag Stuttgart: New York, Hetarenes, Vol. E8b, III, p. 764 (1994); (b) W. Stadlbauer, in ed.: R. Neier, Science of Synthesis: Indazoles, Georg-Thieme-Verlag Stuttgart: New York, Vol. 2.12.4 (Hetarenes), pp. 227-324 (2002).
Y. Ikeda, N. Takano, H. Matsushita, Y. Shiraki, T. Koide, R. Nagashima, Y. Fujimura, M. Shindo, S. Suzuki and T. Iwasaki, Arzneimittelforschung, 29, 511 (1979).
G. Picciola, F. Ravenna, G. Carenini, P. Gentili and M. Riva, Farmaco Ed. Sci., 36, 1037 (1981).
The Merck Index, edn. 12, S. Budavari, Ed., Merck & Co., Rahway, New Jersey (1996).
L. Mosti, G. Menozzi, P. Fossa, P. Schenone, E. Lampa, C. Parrillo, M. D'Amisco and F. Rossi, Farmaco, 47, 567 (1992).
S. Andronati, V. Sava, S. Makan and G. Kolodeev, Pharmazie, 54, 99 (1999).
V.G. Kharitonov, V.S. Sharma, D. Magde and D. Koesling, Biochemistry, 38, 10699 (1999); doi:10.1021/bi990277f.
(a) J.D. Rodgers, B.L. Johnson, H. Wang, R.A. Greenberg, S. Erickson-Viitanen, R.M. Klabe, B.C. Cordova, M.M. Rayner, G.N. Lam and C.-H. Chang, Bioorg. Med. Chem. Lett., 6, 2919 (1996); doi:10.1016/S0960-894X(96)00531-8; (b) J.-H. Sun, C.A. Teleha, J.-S. Yan, J.D. Rodgers and D.A. Nugiel, J. Org. Chem., 62, 5627 (1997); doi:10.1021/jo970375b.
(a) T. Morie, H. Harada and S. Kato, Synth. Commun., 27, 559 (1997); doi:10.1080/00397919708003326; (b) J. Bermudez, C.S. Fake, G.F. Joiner, K.A. Joiner, F.D. King, W.D. Miner and G.J. Sanger, J. Med. Chem., 33, 1924 (1990); doi:10.1021/jm00169a016.
C. Nofre, J.M. Tinti and F. Quar, FR Patent 26099603 (1988).
M. Negwer, In Organic-Chemical Drugs and their Synonyms: (An Inter-national Survey), Akademie Verlag GmbH: Berlin, edn. 7 (1994).
J.H. Montgomery, In Agrochemicals Desk Reference: Environmental Data, Lewis Publishers, Chelsea, MI (1993).
G. D’Aprano, M. Leclerc, G. Zotti and G. Schiavon, Chem. Mater., 7, 33 (1995); doi:10.1021/cm00049a008.
F. Fache, E. Schulz, M.L. Tommasino and M. Lemaire, Chem. Rev., 100, 2159 (2000); doi:10.1021/cr9902897.
(a) D.M.T. Chan, K.L. Monaco, R.P. Wang and M.P. Winters, Tetrahedron Lett., 39, 2933 (1998); doi:10.1016/S0040-4039(98)00503-6; (b) P.Y.S. Lam, C.G. Clark, S. Saubern, J. Adams, M.P. Winters, D.M.T. Chan and A. Combs, Tetrahedron Lett., 39, 2941 (1998); doi:10.1016/S0040-4039(98)00504-8.
F.Y. Kwong and S.L. Buchwald, Org. Lett., 5, 793 (2003); doi:10.1021/ol0273396.
J.P. Finet, A.Y. Fedorov, S. Combes and G. Boyer, Curr. Org. Chem., 6, 597 (2002); doi:10.2174/1385272023374058.
A.J. Souers, J. Gao, D. Wodka, A.S. Judd, M.M. Mulhern, J.J. Napier, M.E. Brune, E.N. Bush, S.J. Brodjian, B.D. Dayton, R. Shapiro, L.E. Hernandez, K.C. Marsh, H.L. Sham, C.A. Collins and P.R. Kym, Bioorg. Med. Chem. Lett., 15, 2752 (2005); doi:10.1016/j.bmcl.2005.03.114.

References

(a) J. Elguero, in eds.: A.R. Katritzky and C.W. Rees, Comprehensive Heterocyclic Chemistry, Pyrazoles and their Benzo Derivatives, Pergamon Press: Oxford, Vol. 5, pp. 167-303 (1984); (b) J. Elguero, in eds.: A.R. Katritzky, C.W. Rees and E.F.V. Scriven, Comprehensive Heterocyclic Chemistry II: Pyrazoles, Pergamon Press: Oxford, Vol. 3, pp. 1-75 (1996).

(a) W. Stadlbauer, in ed.: E. Schaumann, In Houben-Weyl, Methoden der Organischen Chemie: Indazole (Benzopyrazole); Georg-Thieme-Verlag Stuttgart: New York, Hetarenes, Vol. E8b, III, p. 764 (1994); (b) W. Stadlbauer, in ed.: R. Neier, Science of Synthesis: Indazoles, Georg-Thieme-Verlag Stuttgart: New York, Vol. 2.12.4 (Hetarenes), pp. 227-324 (2002).

Y. Ikeda, N. Takano, H. Matsushita, Y. Shiraki, T. Koide, R. Nagashima, Y. Fujimura, M. Shindo, S. Suzuki and T. Iwasaki, Arzneimittelforschung, 29, 511 (1979).

G. Picciola, F. Ravenna, G. Carenini, P. Gentili and M. Riva, Farmaco Ed. Sci., 36, 1037 (1981).

The Merck Index, edn. 12, S. Budavari, Ed., Merck & Co., Rahway, New Jersey (1996).

L. Mosti, G. Menozzi, P. Fossa, P. Schenone, E. Lampa, C. Parrillo, M. D'Amisco and F. Rossi, Farmaco, 47, 567 (1992).

S. Andronati, V. Sava, S. Makan and G. Kolodeev, Pharmazie, 54, 99 (1999).

V.G. Kharitonov, V.S. Sharma, D. Magde and D. Koesling, Biochemistry, 38, 10699 (1999); doi:10.1021/bi990277f.

(a) J.D. Rodgers, B.L. Johnson, H. Wang, R.A. Greenberg, S. Erickson-Viitanen, R.M. Klabe, B.C. Cordova, M.M. Rayner, G.N. Lam and C.-H. Chang, Bioorg. Med. Chem. Lett., 6, 2919 (1996); doi:10.1016/S0960-894X(96)00531-8; (b) J.-H. Sun, C.A. Teleha, J.-S. Yan, J.D. Rodgers and D.A. Nugiel, J. Org. Chem., 62, 5627 (1997); doi:10.1021/jo970375b.

(a) T. Morie, H. Harada and S. Kato, Synth. Commun., 27, 559 (1997); doi:10.1080/00397919708003326; (b) J. Bermudez, C.S. Fake, G.F. Joiner, K.A. Joiner, F.D. King, W.D. Miner and G.J. Sanger, J. Med. Chem., 33, 1924 (1990); doi:10.1021/jm00169a016.

C. Nofre, J.M. Tinti and F. Quar, FR Patent 26099603 (1988).

M. Negwer, In Organic-Chemical Drugs and their Synonyms: (An Inter-national Survey), Akademie Verlag GmbH: Berlin, edn. 7 (1994).

J.H. Montgomery, In Agrochemicals Desk Reference: Environmental Data, Lewis Publishers, Chelsea, MI (1993).

G. D’Aprano, M. Leclerc, G. Zotti and G. Schiavon, Chem. Mater., 7, 33 (1995); doi:10.1021/cm00049a008.

F. Fache, E. Schulz, M.L. Tommasino and M. Lemaire, Chem. Rev., 100, 2159 (2000); doi:10.1021/cr9902897.

(a) D.M.T. Chan, K.L. Monaco, R.P. Wang and M.P. Winters, Tetrahedron Lett., 39, 2933 (1998); doi:10.1016/S0040-4039(98)00503-6; (b) P.Y.S. Lam, C.G. Clark, S. Saubern, J. Adams, M.P. Winters, D.M.T. Chan and A. Combs, Tetrahedron Lett., 39, 2941 (1998); doi:10.1016/S0040-4039(98)00504-8.

F.Y. Kwong and S.L. Buchwald, Org. Lett., 5, 793 (2003); doi:10.1021/ol0273396.

J.P. Finet, A.Y. Fedorov, S. Combes and G. Boyer, Curr. Org. Chem., 6, 597 (2002); doi:10.2174/1385272023374058.

A.J. Souers, J. Gao, D. Wodka, A.S. Judd, M.M. Mulhern, J.J. Napier, M.E. Brune, E.N. Bush, S.J. Brodjian, B.D. Dayton, R. Shapiro, L.E. Hernandez, K.C. Marsh, H.L. Sham, C.A. Collins and P.R. Kym, Bioorg. Med. Chem. Lett., 15, 2752 (2005); doi:10.1016/j.bmcl.2005.03.114.

Issue

Vol. 26 No. 22 (2014): Vol 26 Issue 22

Synthesis of Novel N-Aryl-1H-indazolamines from Amino-1H-indazoles and Arylboronic Acids

Corresponding Author(s) : Udutha Kumara Swamy

Abstract

Keywords

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