One-Pot Synthesis of Dibenzo[b,e][1,4]diazepin-1-ones

Monica Nardi; Annalisa Cozza; Antonio De Nino; Manuela Oliverio; Antonio Procopio

doi:10.1055/s-0031-1289691

PAPER

One-Pot Synthesis of Dibenzo[b,e][1,4]diazepin-1-ones

Monica Nardi*^a, Annalisa Cozza^a, Antonio De Nino^a, Manuela Oliverio^b, Antonio Procopio^b
^a Dipartimento di Chimica, Università della Calabria, ponte Bucci cubo 12/c, 87030 Arcavacata di Rende (Cs), Italy
Fax: +39(0984)493077; e-Mail: nardi@unical.it;
^b Dipartimento di Scienze Farmacobiologico, Università Magna Græcia di Catanzaro, Complesso Ninì Barbieri, 88021 Roccelletta di Borgia (CZ), Italy

Abstract

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Abstract

A simple and efficient method for the synthesis of wide range of 3,3-dimethyl-11-alkyl or aryl 2,3,4,5-tetrahydro-1H-dibenzo[b,e][1,4]diazepin-1-ones, recently reported as hepatitis C virus (HCV) NS5B polymerase inhibitors, is presented. The proposed method consists of one-pot condensation between 1,2-phenylenediamine and 5,5-dimethylcyclohexane-1,3-dione (dimedone) followed by cyclization with various alkyl and aryl acyl chlorides catalyzed by Er(III) triflate. With respect to methods previously reported, the proposed one-pot procedure furnishes appreciably higher yield of product in shorter reaction time.

Key words

amines - azo compounds - drugs - Lewis acids - lanthanides

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References

1a Schutz H. Benzodiazepines Springer; Heidelberg: 1982.

1b Landquist JK. In Comprehensive Heterocyclic Chemistry Vol. 1: Katritzky AR. Rees CW. Pergamon; Oxford: 1984. p.166-170

2a Fryer RI. Bicyclic Diazepines, In Comprehensive Heterocyclic Chemistry Vol. 50: Taylor EC. Wiley; New York: 1991. Chap. II.

2b Kavita DT. Achaiah G. Reddy VMH. J. Indian Chem. Soc. 1988, 65: 567

2c Narayana B. Vijaya Raj KK. Ashalatha BV. Suchetha KN. Eur. J. Med. Chem. 2006, 41: 417

3a For a review, see: Gante J. Angew. Chem., Int. Ed. Engl. 1994, 33: 1699

3b Gutierrez CD, Termin A, Joshi P, HadidaRuah S, Bergeron D, Yoo S, and Cao J. inventors; Patent WO 2008011190. ; Chem. Abstr. 2008, 148, 191944

3c Goldstein SW, Longo KP, Nagel AA, and Lowe JA. inventors; US Patent US 6319915. ; Chem. Abstr. 2001, 135, 366727

3d Jaquith J. inventors; Patent WO 2007101347. ; Chem. Abstr. 1998, 129, 54607

3e Golec JMC, Lauffer DJ, Livingston DJ, Mullican MD, Nyce PL, Robidoux ALC, and Wannamaker MW. inventors; Patent WO 9824804. ; Chem. Abstr. 2007, 147, 365786

3f Amblard M. Daffix I. Bedos P. Bergé G. Pruneau D. Paquet J.-L. Luccarini J.-M. Bélichard P. Dodey P. Martinez J. J. Med. Chem. 1999, 42: 4185

3g Pruneau D. Paquet J.-L. Luccarini J.-M. Bélichard P. Martinez J. J. Med. Chem. 1999, 42: 4193

3h Gan J. Ma D. Org. Lett. 2009, 11: 2788

4a Kosychova L. Stumbreviciute Z. Pleckaitiene L. Janciene R. Puodziunaite BD. Chem. Heterocycl. Comp. 2004, 40: 811

4b Janciene R. Vektariene A. Stumbreviciute Z. Kochychova L. Klimavicius AA. Heteroat. Chem. 2004, 15: 363

4c Kosychova L. Pleckaitiene L. Staniulyte Z. Janciene R. Palaima A. Puodziunaite BD. ARKIVOC 2006, (xiii): 158

4d Che X. Zheng L. Dang Q. Bai X. Tetrahedron 2006, 62: 2563

4e Terret NK. Bojanic D. Merson JR. Stephenson PT. Bioorg. Med. Chem. Lett. 1992, 2: 1745

5a Nyanguile O. Pauwels F. Van den Broeck W. Boutton CW. Quirynen L. Ivens T. Van der Helm L. Vandercruyssen G. Mostmans W. Delouvroy F. Dehertogh P. Cummings MD. Bonfanti J.-F. Simmen KA. Raboisson P. Antimicrob. Agents Chemother. 2008, 52: 4420

5b McGowan D. Nyanguile O. Cummings MD. Vendeville S. Vandyck K. Van den Broeck W. Boutton CW. De Bondt H. Quirynen L. Amssoms K. Bonfanti J.-F. Last S. Rombauts K. Tahri A. Hu 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

6a Balakrishna MS. Kaboudin B. Tetrahedron Lett. 2001, 42: 1127

6b Curini M. Epifano F. Marcotullio MC. Rosati O. Tetrahedron Lett. 2001, 42: 3193

6c Herbert JAL. Suschitzky H. J. Chem. Soc., Perkin Trans. 1 1974, 2657

6d Jarikote DV. Siddiqui SA. Rajgopal R. Thoma D. Lahoti RJ. Srinivasan KV. Tetrahedron Lett. 2003, 44: 1835

6e Yadav JS. Reddy BVS. Praveenkumar S. Nagaiah K. Lingaiah N. Saiprasad PS. Synthesis 2004, 901

6f Pan X.-Q. Zou J.-P. Huang Z.-H. Zhang W. Tetrahedron Lett. 2008, 49: 5302

6g Sharma SD. Gogoi P. Konwar D. Green Chem. 2007, 9: 153

6h Suryakiran N. Rajesh K. Prabhakar P. Selvam JJP. Venkateswarlu Y. Catal. Commun. 2007, 8: 1635

6i Sarda SR. Jadhav WN. Kolhe NB. Landge MG. Pawar RP. J. Iran. Chem. Soc. 2009, 6: 477

6j Sanghetti JN. Kokare ND. Shinde DB. Chin. Chem. Lett. 2007, 18: 1305

7a Matsuo K. Yoshida M. Ohta M. Tanaka K. Chem. Pharm. Bull. 1985, 33: 4057

7b Tonkikh NN. Strakovs KV. Petrova MV. Chem. Heterocycl. Comp. 2004, 40: 949

7c Cortés Cortés E. Valencia Cornejo AL. García-Mellado de Cortés O. J. Heterocycl. Chem. 2007, 44: 183

7d Bennamane N. Kaoua R. Hammal L. Nedjar-Kolli B. Org. Commun. 2008, 1: 62

8a Procopio A. Gaspari M. Nardi M. Oliverio M. Rosati O. Tetrahedron Lett. 2008, 49: 2289

8b Procopio A. Gaspari M. Nardi M. Oliverio M. Romeo R. Tetrahedron Lett. 2008, 49: 1961

8c Bartoli G. Dalpozzo R. De Nino A. Maiuolo L. Nardi M. Procopio A. Tagarelli A. Eur. J. Org. Chem. 2004, 2176

8d Procopio A. Gaspari M. Nardi M. Oliverio M. Tagarelli A. Sindona G. Tetrahedron Lett. 2007, 48: 8623

8e Procopio A. Dalpozzo R. De Nino A. Maiuolo L. Nardi M. Russo B. Adv. Synth. Catal. 2005, 347: 1447

8f Procopio A. Costanzo P. Dalpozzo R. Maiuolo L. Nardi M. Oliverio M. Tetrahedron Lett. 2010, 51: 5150

9 Cozza A. Maiuolo L. Nardi M. Oliverio M. Procopio A. Tetrahedron Lett. 2011, 52: 4827

10a Anastas PT. Warner JC. Green Chemistry: Theory and Practice Oxford Science Publications; Oxford: 1998.

10b Collins TC. Green Chemistry: Frontiers in Chemical Synthesis and Processes Oxford University Press; Oxford: 1998.

10c Tundo P. Anastas P. Black DS. Breen J. Collins T. Memoli S. Miyamoto J. Polyakoff M. Tumas W. Pure Appl. Chem. 2000, 72: 1207

10d Anastas PT. Kirchhoff MM. Acc. Chem. Res. 2002, 35: 68