Facile Preparation of 6-(Aminomethyl)isoindolin-1-one Realizing Complete Reduction of Double Aromatic Cyano Groups

Lei Bi; Chenchao Fu; Lei Yao

doi:10.14233/ajchem.2014.17169

Issue

Vol. 26 No. 19 (2014): Vol 26 Issue 19

Issue Published : September 16, 2014

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

Facile Preparation of 6-(Aminomethyl)isoindolin-1-one Realizing Complete Reduction of Double Aromatic Cyano Groups

https://doi.org/10.14233/ajchem.2014.17169

Lei Bi

School of Chemistry and Chemical Engineering, Anhui University of Technology, 59 Hudong Road, Maanshan 243002, Anhui, P.R. China

Chenchao Fu

School of Chemistry and Chemical Engineering, Anhui University of Technology, 59 Hudong Road, Maanshan 243002, Anhui, P.R. China

Lei Yao

School of Pharmacy, Yantai University, 32 Qingquan Road, Yantai, Shandong 264005, P.R. China

Corresponding Author(s) : Lei Bi

lei_bi@hotmail.com

Asian Journal of Chemistry, Vol. 26 No. 19 (2014): Vol 26 Issue 19
Article Published : September 19, 2014

Abstract

6-(Aminomethyl)isoindolin-1-one is a key intermediate enroute to many investigational therapeutic agents. The need for it prompts a concise synthesis, which includes; (1) cyanation without using costly transition metal catalysts; (2) complete hydrogenation of the resulting dicyanide. This synthetic route emphasizes high atom-efficiency and simple operation. 5-(Aminomethyl)isoindolin-1-one, a structural analogue, is synthesized via this route as well.

Keywords

Isoindoline Complete reduction Dicyanide

Bi, L., Fu, C., & Yao, L. (2014). Facile Preparation of 6-(Aminomethyl)isoindolin-1-one Realizing Complete Reduction of Double Aromatic Cyano Groups. Asian Journal of Chemistry, 26(19), 6655–6657. https://doi.org/10.14233/ajchem.2014.17169

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References

E. Valencia, A.J. Freyer, M. Shamma and V. Fajardo, Tetrahedron Lett., 25, 599 (1984); doi:10.1016/S0040-4039(00)99948-9.
E. Valencia, V. Fajardo, A.J. Freyer and M. Shamma, Tetrahedron Lett., 26, 993 (1985); doi:10.1016/S0040-4039(00)98494-6.
T.L. Stuk, B.K. Assink, D.T. Bates, D.T. Erdman, V. Fedij, S.M. Jennings, J.A. Lassig, R.J. Smith and T.L. Smith, Org. Process Res. Dev., 7, 851 (2003); doi:10.1021/op034060b.
B. Portevin, C. Tordjman, P. Pastoureau, J. Bonnet and G. De Nanteuil, J. Med. Chem., 43, 4582 (2000); doi:10.1021/jm990965x.
Y. Zhou, E. Bourque, Y. Zhu, E. Mceachern, C. Harwig, R. Skerlj, G. Bridger, T.-S. Li and M. Metz, Chemokine Receptor Binding Compounds, U.S. Patent WO/2007/022371 (2007).
D. Zhou and J. Gross, Isoquinolinyl and Isoindolinyl Derivatives as Histamine-3 Antagonists, U.S. Patent WO/2009/036144 (2009).
G. Muller and A. Ruchelman, Isoindoline Compounds for Use in the Treatment of Cancer, U.S. Patent WO/2010/053732 (2010).
G. Muller, R. Chen and A. Ruchelman, 5-Substituted Isoindoline Compounds, U.S. Patent WO/2008/027542 (2008).
D.L. Priebbenow, S.G. Stewart and F.M. Pfeffer, Org. Biomol. Chem., 9, 1508 (2011); doi:10.1039/c0ob00835d.
J. Harris, S. Neelamkavil, B. Neustadt, C. Boyle, H. Liu, J. Hao, A. Stamford, S. Chackalamannil and W. Greenlee, Bicyclic Heterocycle Derivatives and Use Thereof as Gpr119 Modulators, U.S. Patent WO/2009/143049 (2009).
G.W. Muller and A.L. Ruchelman, Isoindoline Compounds and Methods of Their Use, U.S. Patent 8222249 (2012).
M.D. Clift and R.B. Silverman, Bioorg. Med. Chem. Lett., 18, 3122 (2008); doi:10.1016/j.bmcl.2007.10.060.
N. Wurtz, E. Priestley, D. Cheney, P. Glunz, X. Zhang, V. Ladziata, B. Parkhurst and L. Mueller, Macrocyclic Factor Viia Inhibitors Useful as Anticoagulants, U.S. Patent WO/2008/079836 (2008).
X. Zhang, A.A. Nirschl, Y. Zou and E.S. Priestley, Phenylglycinamide and Pyridylglycinamide Derivatives Useful as Anticoagulants, U.S. Patent WO/2007/002313 (2007).
D.C.M. Leysen, O.R. Defert, J.O.A. De Kerpel, E.P.P.R. Fourmaintraux, P. Arzel and G.J.H. De Wilde, Kinase Inhibitors, U.S. Patent WO/2005/082367 (2005).
J. Corsi, S.E. Diamond, J.E. Galle, F. Mares and F.J. Regina, Selective Hydrogenation of Aliphatic Dinitriles to Omega-Aminonitriles in Ammonia with Supported, Finely Dispersed Rhodium-Containing Catalyst, U.S. Patent US4601859 A (1986).
M. Laronze, M. Boisbrun, S. Léonce, B. Pfeiffer, P. Renard, O. Lozach, L. Meijer, A. Lansiaux, C. Bailly, J. Sapi and J.-Y. Laronze, Bioorg. Med. Chem., 13, 2263 (2005); doi:10.1016/j.bmc.2004.12.045.
T.D. Nelson, C.R. LeBlond, D.E. Frantz, L. Matty, J.V. Mitten, D.G. Weaver, J.C. Moore, J.M. Kim, R. Boyd, P.-Y. Kim, K. Gbewonyo, M. Brower, M. Sturr, K. McLaughlin, D.R. McMasters, M.H. Kress, J.M. McNamara and U.H. Dolling, J. Org. Chem., 69, 3620 (2004); doi:10.1021/jo035794p.

References

E. Valencia, A.J. Freyer, M. Shamma and V. Fajardo, Tetrahedron Lett., 25, 599 (1984); doi:10.1016/S0040-4039(00)99948-9.

E. Valencia, V. Fajardo, A.J. Freyer and M. Shamma, Tetrahedron Lett., 26, 993 (1985); doi:10.1016/S0040-4039(00)98494-6.

T.L. Stuk, B.K. Assink, D.T. Bates, D.T. Erdman, V. Fedij, S.M. Jennings, J.A. Lassig, R.J. Smith and T.L. Smith, Org. Process Res. Dev., 7, 851 (2003); doi:10.1021/op034060b.

B. Portevin, C. Tordjman, P. Pastoureau, J. Bonnet and G. De Nanteuil, J. Med. Chem., 43, 4582 (2000); doi:10.1021/jm990965x.

Y. Zhou, E. Bourque, Y. Zhu, E. Mceachern, C. Harwig, R. Skerlj, G. Bridger, T.-S. Li and M. Metz, Chemokine Receptor Binding Compounds, U.S. Patent WO/2007/022371 (2007).

D. Zhou and J. Gross, Isoquinolinyl and Isoindolinyl Derivatives as Histamine-3 Antagonists, U.S. Patent WO/2009/036144 (2009).

G. Muller and A. Ruchelman, Isoindoline Compounds for Use in the Treatment of Cancer, U.S. Patent WO/2010/053732 (2010).

G. Muller, R. Chen and A. Ruchelman, 5-Substituted Isoindoline Compounds, U.S. Patent WO/2008/027542 (2008).

D.L. Priebbenow, S.G. Stewart and F.M. Pfeffer, Org. Biomol. Chem., 9, 1508 (2011); doi:10.1039/c0ob00835d.

J. Harris, S. Neelamkavil, B. Neustadt, C. Boyle, H. Liu, J. Hao, A. Stamford, S. Chackalamannil and W. Greenlee, Bicyclic Heterocycle Derivatives and Use Thereof as Gpr119 Modulators, U.S. Patent WO/2009/143049 (2009).

G.W. Muller and A.L. Ruchelman, Isoindoline Compounds and Methods of Their Use, U.S. Patent 8222249 (2012).

M.D. Clift and R.B. Silverman, Bioorg. Med. Chem. Lett., 18, 3122 (2008); doi:10.1016/j.bmcl.2007.10.060.

N. Wurtz, E. Priestley, D. Cheney, P. Glunz, X. Zhang, V. Ladziata, B. Parkhurst and L. Mueller, Macrocyclic Factor Viia Inhibitors Useful as Anticoagulants, U.S. Patent WO/2008/079836 (2008).

X. Zhang, A.A. Nirschl, Y. Zou and E.S. Priestley, Phenylglycinamide and Pyridylglycinamide Derivatives Useful as Anticoagulants, U.S. Patent WO/2007/002313 (2007).

D.C.M. Leysen, O.R. Defert, J.O.A. De Kerpel, E.P.P.R. Fourmaintraux, P. Arzel and G.J.H. De Wilde, Kinase Inhibitors, U.S. Patent WO/2005/082367 (2005).

J. Corsi, S.E. Diamond, J.E. Galle, F. Mares and F.J. Regina, Selective Hydrogenation of Aliphatic Dinitriles to Omega-Aminonitriles in Ammonia with Supported, Finely Dispersed Rhodium-Containing Catalyst, U.S. Patent US4601859 A (1986).

M. Laronze, M. Boisbrun, S. Léonce, B. Pfeiffer, P. Renard, O. Lozach, L. Meijer, A. Lansiaux, C. Bailly, J. Sapi and J.-Y. Laronze, Bioorg. Med. Chem., 13, 2263 (2005); doi:10.1016/j.bmc.2004.12.045.

T.D. Nelson, C.R. LeBlond, D.E. Frantz, L. Matty, J.V. Mitten, D.G. Weaver, J.C. Moore, J.M. Kim, R. Boyd, P.-Y. Kim, K. Gbewonyo, M. Brower, M. Sturr, K. McLaughlin, D.R. McMasters, M.H. Kress, J.M. McNamara and U.H. Dolling, J. Org. Chem., 69, 3620 (2004); doi:10.1021/jo035794p.

Issue

Vol. 26 No. 19 (2014): Vol 26 Issue 19

Facile Preparation of 6-(Aminomethyl)isoindolin-1-one Realizing Complete Reduction of Double Aromatic Cyano Groups

Corresponding Author(s) : Lei Bi

Abstract

Keywords

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