Efficient, environmentally benign, one-pot procedure for the synthesis of 1, 5-benzodiazepine derivatives using N-methyl-2-pyrrolidonium hydrogen sulphate as an ionic liquid catalyst under solvent-free conditions

doi:10.1016/S1872-2067(14)60304-1

催化学报 ›› 2015, Vol. 36 ›› Issue (5): 734-741.DOI: 10.1016/S1872-2067(14)60304-1

Efficient, environmentally benign, one-pot procedure for the synthesis of 1, 5-benzodiazepine derivatives using N-methyl-2-pyrrolidonium hydrogen sulphate as an ionic liquid catalyst under solvent-free conditions

Hossein Naeimi, Hossein Foroughi

Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, 87317, Iran

收稿日期:2014-12-22 修回日期:2015-01-23 出版日期:2015-04-17 发布日期:2015-04-17
通讯作者: Hossein Naeimi

Efficient, environmentally benign, one-pot procedure for the synthesis of 1, 5-benzodiazepine derivatives using N-methyl-2-pyrrolidonium hydrogen sulphate as an ionic liquid catalyst under solvent-free conditions

Hossein Naeimi, Hossein Foroughi

Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, 87317, Iran

Received:2014-12-22 Revised:2015-01-23 Online:2015-04-17 Published:2015-04-17
Contact: Hossein Naeimi

摘要/Abstract

摘要：

A powerful and environmentally benign method has been developed for the one-pot synthesis of 4-substituted-1,5-benzodiazepines via the three-component reaction of a series of aldehydes with dimedone and o-phenylenediamine using [H-NMP][HSO₄] as a Brönsted acidic ionic liquid catalyst under solvent-free conditions. The key benefits of this new method over existing techniques include high yields, the use of a green catalyst, short reaction times and facile catalyst separation.

关键词: Ionic liquid, Benzodiazepine, Solvent-free conditions, Dimedone

Abstract:

Key words: Ionic liquid, Benzodiazepine, Solvent-free conditions, Dimedone

Hossein Naeimi, Hossein Foroughi. Efficient, environmentally benign, one-pot procedure for the synthesis of 1, 5-benzodiazepine derivatives using N-methyl-2-pyrrolidonium hydrogen sulphate as an ionic liquid catalyst under solvent-free conditions[J]. 催化学报, 2015, 36(5): 734-741.

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参考文献

[1] Shorter E. Benzodiazepines. A Historical Dictionary of Psychiatry. New York: Oxford University Press, 2005. 41
[2] Bremner J B, Samosorn S. In: Newkome G R ed. Comprehensive Heterocyclic Chemistry III. Amsterdam: Elsevier, 2008
[3] Riemann D, Perlis M L. Sleep Med Rev, 2009, 13: 205
[4] Cortes E C, Cornejo A L, Garcia-Mellado de Cortes O. J Heterocycl Chem, 2007, 44: 183
[5] Makaron L, Moran C A, Namjoshi O, Rallapalli S, Cook J M, Rowlett J K. Pharmacol Biochem Behav, 2013, 104: 62
[6] Allison C, Pratt J A. Pharmacol Therapeut, 2003, 98: 171
[7] Hawkins E J, Malte C A, Imel Z E, Saxon A J, Kivlahan D R. Drug Alcohol Depend, 2012, 124: 154
[8] McGowan D, Nyanguile O, Cummings M D, Vendeville S, Vandyck K, Van-den Broeck W, Boutton C W, De Bondt H, Quirynen L, Amssoms K, Bonfanti J F, Last S, Rombauts K, Tahri A, Hu L L, Delouvroy F, Vermeiren K, Vandercruyssen G, Van der Helm L, Cleiren E, Mostmans W, Lory P, Pille G, Van Emelen K, Fanning G, Pauwels F, Lin T I, Simmen K, Raboisson P. Bioorg Med Chem Lett, 2009, 19: 2492
[9] Schimer J, Cigler P, Vesely J, Grantz-Saskova K, Lepsik M, Brynda J, Rezacova P, Kozisek M, Cisarova I, Oberwinkler H, Kraeusslich H G, Konvalinka J. J Med Chem, 2012, 55: 10130
[10] Fader L D, Bethell R, Bonneau P, Boes M, Bousquet Y, Cordingley M G, Coulombe R, Deroy P, Faucher A M, Gagnon A, Goudreau N, Grand-Maitre C, Guse I, Hucke O, Kawai S H, Lacoste J E, Landry S, Lemke C T, Malenfant E, Mason S, Morin S, O'Meara J, Simoneau B, Titolo S, Yoakim C. Bioorg Med Chem Lett, 2011, 21: 398
[11] Leggio L, Kenna G A, Swift R M. Prog Neuro-Psychopharm Biol Psych, 2008, 32: 1106
[12] Kodomari M, Noguchi T, Aoyama T. Synth Commun, 2004, 34: 1783
[13] Maiti G, Kayal U, Karmakar R, Bhattacharya R N. Tetrahedron Lett, 2012, 53: 1460
[14] Yi W B, Cai C. J Fluorine Chem, 2009, 130: 1054
[15] Xu J X, Zuo G, Chan W L. Heteroatom Chem, 2001, 12: 636
[16] Uchida H, Suzuki T, Mamo D C, Mulsant B H, Kikuchi T, Takeuchi H, Tomita M, Watanabe K, Yagi G, Kashima H. J Anxiety Disord, 2009, 23: 477
[17] Leonard B E. Human Psychopharmacol, 1999, 14: 125
[18] Holbrook A M, Crowther R, Lotter A, Cheng C, King D. Can Med Assoc J, 2000, 162: 225
[19] Pan X Q, Zou J P, Huang Z H; Zhang W. Tetrahedron Lett, 2008, 49: 5302
[20] Sangshetti J N, Chouthe R S, Jadhav M R, Sakle N S, Chabukswar A, Gonjari I, Darandale S, Shinde D B. Arab J Chem, 2013, doi:10.1016/j.arabjc.2013.04.004
[21] Cortes E C, Banos M A, Garcia-Mellado De Cortes O. J Heterocycl Chem, 2004, 41: 277
[22] Gurkovskii A L, Tonkikh N N, Petrova M V, Strakov A Y. Chem Heterocycl Compd, 1999, 35: 625
[23] Strakov A Y, Petrova M V, Tonkikh N N, Gurkovskii A I, Popelis Y, Kreishman G P, Belyakov S V. Chem Heterocycl Compd, 1997, 33: 321
[24] Tolpygin I E, Mikhailenko N V, Bumber A A, Shepelenko E N, Revinsky U V, Dubonosov A D, Bren V A, Minkin V I. Russ J Gen Chem, 2012, 82: 1243
[25] Tonkikh N N, Strakovs A Y, Rizhanova K V, Petrova M V. Chem Heterocycl Compd, 2004, 40: 949
[26] Jiang B, Li Q Y, Zhang H, Tu S J, Pindi S, Li G G. Org Lett, 2012, 14: 700
[27] Wang S L, Cheng C, Wu F Y, Jiang B, Shi F, Tu S J, Rajale T, Li G G. Tetrahedron, 2011, 67: 4485
[28] Zhu J P, Bienayme H. Multicomponent Reactions. Weinheim: Wiley-VCH, 2005
[29] Kumaravel K, Vasuki G. Curr Org Chem, 2009, 13: 1820
[30] Tietze L F, Bell H P, Brasche G. Domino Reactions in Organic Synthesis. Weinheim: Wiley-VCH, 2006
[31] Terrett N K. Combinatorial Chemistry. New York: Oxford University Press, 1998
[32] Chanda A, Fokin V V. Chem Rev, 2009, 109: 725
[33] Pirrung M C, Das Sarma K. J Am Chem Soc, 2004, 126: 444
[34] Dupont J, de Souza R F, Suarez P A Z. Chem Rev, 2002, 102: 3667
[35] Itoh H, Naka K, Chujo Y. J Am Chem Soc, 2004: 126: 3026
[36] Yue C B, Fang D, Liu L, Yi T F. J Mol Liq, 2011, 163: 99
[37] Naeimi H, Nazifi Z S. C R Chim, 2014, 17: 41
[38] Naeimi H, Nazifi Z S. J Ind Eng Chem, 2014, 20: 1043
[39] Shaterian H R, Ranjbar M. J Mol Liq, 2011, 160: 40
[40] Liu W W, Cheng L Y, Zhang Y M, Wang H P, Yu M F. J Mol Liq, 2008, 140: 68
[41] Tong X L, Li Y D. ChemSusChem, 2010, 3: 350
[42] Xie C X, Li H L, Li L, Yu S, Liu F S. J Hazard Mater, 2008, 151: 847
[43] Arellano M del R, Martinez R, Cortes E. J Heterocycl Chem, 1982, 19: 321

Efficient, environmentally benign, one-pot procedure for the synthesis of 1, 5-benzodiazepine derivatives using N-methyl-2-pyrrolidonium hydrogen sulphate as an ionic liquid catalyst under solvent-free conditions

Efficient, environmentally benign, one-pot procedure for the synthesis of 1, 5-benzodiazepine derivatives using N-methyl-2-pyrrolidonium hydrogen sulphate as an ionic liquid catalyst under solvent-free conditions

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