Investigation of Various Organocatalysts for Improved and Efficient One Pot Synthesis of 2,3-Dihydro-1H-1,5-benzodiazepines Under Solvent-Free Condition

Yuhao Zhao; Shikha Sharma; Minghua Huang; Akshdeep Sandhar; Rajesh K. Singh; Yanxu Ma

doi:10.14233/ajchem.2014.16440

Issue

Vol. 26 No. 16 (2014): Vol 26 Issue 16

Issue Published : July 28, 2014

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

Investigation of Various Organocatalysts for Improved and Efficient One Pot Synthesis of 2,3-Dihydro-1H-1,5-benzodiazepines Under Solvent-Free Condition

https://doi.org/10.14233/ajchem.2014.16440

Yuhao Zhao

School of Traditional Chinese Medicine, Capital Medical University, Beijing 100069, P.R. China;Authors contributed equally this work

Shikha Sharma

Department of Pharmaceutical Chemistry, Shivalik College of Pharmacy (Under Local Govt. Dept. Punjab) Nangal, Distt. Rupnagar- 140126, Punjab, India ; Authors contributed equally this work

Minghua Huang

Department of Orthopedics, Beijing Traditional Chinese Medicine Hospital, Capital Medical University, Beijing 100010, P.R. China

Akshdeep Sandhar

Department of Pharmaceutical Chemistry, Shivalik College of Pharmacy (Under Local Govt. Dept. Punjab) Nangal, Distt. Rupnagar- 140126, Punjab, India

Rajesh K. Singh

Department of Pharmaceutical Chemistry, Shivalik College of Pharmacy (Under Local Govt. Dept. Punjab) Nangal, Distt. Rupnagar- 140126, Punjab, Indi

Yanxu Ma

Department of Orthopedics, Beijing Traditional Chinese Medicine Hospital, Capital Medical University, Beijing 100010, P.R. China

Corresponding Author(s) : Rajesh K. Singh

rksingh244@gmail.com

Asian Journal of Chemistry, Vol. 26 No. 16 (2014): Vol 26 Issue 16
Article Published : August 4, 2014

Abstract

A series of 2,3-dihydro-1H-1,5-benzodiazepines derivatives were synthesized by one-pot three-components condensation reaction of o-phenylenediamines with a,b-unsaturated carbonyl compounds and effect of various Brønsted organo acids as catalyst was studied. Among the various organo acids screened, trifluoroacetic acid is versatile catalyst and the corresponding products were obtained in good to excellent yield (84-94 %) under solvent-free condition.

Keywords

Organoacids Trifluoroacetic acid One pot Solvent-free Green chemistry 1,5-Benzodiazepines

Zhao, Y., Sharma, S., Huang, M., Sandhar, A., K. Singh, R., & Ma, Y. (2014). Investigation of Various Organocatalysts for Improved and Efficient One Pot Synthesis of 2,3-Dihydro-1H-1,5-benzodiazepines Under Solvent-Free Condition. Asian Journal of Chemistry, 26(16), 5116–5120. https://doi.org/10.14233/ajchem.2014.16440

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References

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H. Schutz, Benzodiazepines, Springer: Heidelberg (1982).
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F. Stauffer and R. Neier, Org. Lett., 2, 3535 (2000); doi:10.1021/ol0063205.
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M. Fodili, M. Amari, B. Kolli, A. Robert, M. Baudy-Floch and P. Le Grel, Synthesis, 811 (1999); doi:10.1055/s-1999-3479.
R. Kaoua, N. Bennamane, S. Bakhta, S. Benadji, C. Rabia and B. Nedjar-Kolli, Molecules, 16, 92 (2011); doi:10.3390/molecules16010092.
K.F. Eidman and P.J. Nicholas, in ed.: L. Paquette; TFA: In Encyclopedia of Reagents for Organic Synthesis, Wiley, New York (2004).
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References

L.O. Randall and M. Gordon, Psychopharmacological Agents, Academic Press, New York, vol. 3, pp. 175-281 (1974).

H. Schutz, Benzodiazepines, Springer: Heidelberg (1982).

R. Varala, R. Enugala and S.R. Adapa, J. Braz. Chem. Soc., 18, 291 (2007); doi:10.1590/S0103-50532007000200008.

R. Kumar, P. Chaudhary, S. Nimesh, A.K. Verma and R. Chandra, Green Chem., 8, 519 (2006); doi:10.1039/b601993e.

A. Kamal, N. Shankaraiah, S. Prabhakar, C.R. Reddy, N. Markandeya, K.L. Reddy and V. Devaiah, Bioorg. Med. Chem. Lett., 18, 2434 (2008); doi:10.1016/j.bmcl.2008.02.047.

D.V. Jarikote, S.A. Siddiqui, R. Rajagopal, T. Daniel, R.J. Lahoti and K.V. Srinivasan, Tetrahedron Lett., 44, 1835 (2003); doi:10.1016/S0040-4039(03)00096-0.

S. Ahmad and M. Ali, Iran J. Chem. Eng., 26, 93 (2007).

B. Das, R. Ramu, B. Ravikanth and V. Saidi Reddy, J. Mol. Catal. Chem., 246, 76 (2006); doi:10.1016/j.molcata.2005.10.015.

J.N. Sangshetti, N.D. Kokare and D.B. Shinde, Chin. Chem. Lett., 18, 1305 (2007); doi:10.1016/j.cclet.2007.09.022.

R. Kumar and Y.C. Joshi, ARKIVOC, 142 (2007); doi:10.3998/ark.5550190.0008.d17.

H. Thakuria, A. Pramanik, B.M. Borah and G. Das, Tetrahedron Lett., 47, 3135 (2006); doi:10.1016/j.tetlet.2006.02.137.

M. Pozarentzi, J. Stephanidou-Stephanatou and C.A. Tsoleridis, Tetrahedron Lett., 43, 1755 (2002); doi:10.1016/S0040-4039(02)00115-6.

P.I. Dalko and L. Moisan, Angew. Chem. Int. Ed., 40, 3726 (2001); doi:10.1002/1521-3773(20011015)40:20<3726::AID-ANIE3726>3.0.CO;2-D.

(a) R. Duvedi and R.K. Singh, Asian J. Chem., 24, 5665 (2012); (b) A. Sandhar, D.N. Prasad and R.K. Singh, Indian J. Heterocycl. Chem., 21, 369 (2012); (c) A. Sandhar, D. Nandan Pra, A. Kapoor and R. K. Singh, Curr. Res. Chem., 4, 68 (2012); doi:10.3923/crc.2012.68.75.; (d) A. Sandhar and R.K. Singh, Asian J. Chem., 24, 5643 (2012); (e) A. Sandhar and R.K. Singh, Chem. Sci. Trans., 2, 176 (2012); doi:10.7598/cst2013.315; (f) S. Sharma, D.N. Prasad and R.K. Singh, J. Chem. Pharm. Res., 3, 382 (2011); (g) S. Malik, S. Sharma and R.K. Singh, Asian J. Chem., 24, 5669 (2012); (h) P. Kaur, H. Sharma, R. Rana, D.N. Prasad and R.K. Singh, Asian J. Chem., 24, 5649 (2012); (i) P. Kaur and R.K. Singh, Chem. Sci. Trans., 2(S1), 295 (2013); doi:10.7598/cst2013.443.

F. Stauffer and R. Neier, Org. Lett., 2, 3535 (2000); doi:10.1021/ol0063205.

A. Seifert, U. Scheffler, M. Markert and R. Mahrwald, Org. Lett., 12, 1660 (2010); doi:10.1021/ol100093u.

A. Yokoyama, T. Ohwada and K. Shudo, J. Org. Chem., 64, 611 (1999); doi:10.1021/jo982019e.

B.H. Bhide, V.D. Akolkar and V.G. Prabhu, ChemInform, 23, 35 (1992); doi:10.1002/chin.199235189.

M. Fodili, M. Amari, B. Kolli, A. Robert, M. Baudy-Floch and P. Le Grel, Synthesis, 811 (1999); doi:10.1055/s-1999-3479.

R. Kaoua, N. Bennamane, S. Bakhta, S. Benadji, C. Rabia and B. Nedjar-Kolli, Molecules, 16, 92 (2011); doi:10.3390/molecules16010092.

K.F. Eidman and P.J. Nicholas, in ed.: L. Paquette; TFA: In Encyclopedia of Reagents for Organic Synthesis, Wiley, New York (2004).

(a) M.R. Mohammadizadeh, A. Hasaninejad and M. Bahramzadeh, Synth. Commun., 39, 3232 (2009); doi:10.1080/00397910902737122; (b) S. Fletcher and P.T. Gunning, Tetrahedron Lett., 49, 4817 (2008); doi:10.1016/j.tetlet.2008.06.022; (c) Y.C. Wu, L. Liu, Y.L. Liu, D. Wang and Y.J. Chen, J. Org. Chem., 72, 9383 (2007); doi:10.1021/jo7015604.

Issue

Vol. 26 No. 16 (2014): Vol 26 Issue 16

Investigation of Various Organocatalysts for Improved and Efficient One Pot Synthesis of 2,3-Dihydro-1H-1,5-benzodiazepines Under Solvent-Free Condition

Corresponding Author(s) : Rajesh K. Singh

Abstract

Keywords

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