Nafion-H: An Efficient and Recyclable Heterogeneous Catalyst for the One-Pot Synthesis of 2,3-Disubstituted 4-(3H)-Quinazolinones under Solvent-Free Microwave Irradiation Conditions

Abstract

A one-pot synthesis of 2,3-disubstituted 4-(3H)-quinazolinones has been carried out efficiently by the three-component coupling of isatoic anhydride/anthranilic acid, orthoesters, and amines in the presence of Nafion-H (a perfluorinated resin-supported sulfonic acid) as a heterogeneous catalyst. The reaction occurred within a few minutes under solvent-free microwave irradiation ­conditions to afford the products in good yields. The catalyst was ­recovered and recycled.

Key words

quinazolin-4-(3H)-ones - Nafion-H - one-pot reaction - microwave irradiation

References and Notes

• 1a Terret NK. Gardner M. Gordon DW. Kobylecki RJ. Steele J. Tetrahedron  1995,  51:  8135 
• 1b Armstrong RW. Combs AP. Tempest PA. Brown SD. Keating TA. Acc. Chem. Res.  1996,  29:  123 
• 1c Thomson LA. Ellman JA. Chem. Rev.  1996,  96:  555 
• 1d Tietze LF. Lieb ME. Curr. Opin. Chem. Biol.  1998,  2:  363 
• 1e Domling A. Ugi I. Angew. Chem. Int. Ed.  2000,  39:  3168 
• 2 Green Chemistry, ACS Symposium Series 626   Anastas PT. Williamson TC. American Chemical Society; Washington D.C.: 1996. ; and references therein
• 3 Hall N. Science (Washington, D.C.)  1994,  32:  266 
• 4a Lingaiah BV. Ezikiel G. Yakaiah T. Reddy GV. Rao PS. Tetrahedron Lett.  2006,  47:  4315 
• 4b Lingaiah BPV. Reddy GV. Yakaiah T. Narsaiah B. Reddy SN. Yadla R. Rao PS. Synth. Commun.  2004,  34:  4431 
• 5a Onaka T. Tetrahedron Lett.  1971,  4387 
• 5b Kametani T. Loc CV. Higa T. Koizumi M. Ihara M. Fukumoto K. J. Am. Chem. Soc.  1977,  99:  2306 
• 5c Mori M. Kobayashi H. Kimura M. Ban Y. Heterocycles  1985,  23:  2803 
• 5d Sauter F. Frohlic J. Blasl K. Gewald K. Heterocycles  1985,  40:  851 
• 5e Majo VJ. Perumal PT. Tetrahedron Lett.  1996,  37:  5015 
• 5f Prasad M. Chen L. Repic O. Blacklock TJ. Synth. Commun.  1998,  28:  2125 
• 5g Connolly DJ. Guiry PJ. Synlett  2001,  1707 
• 5h Wang L. Xia J. Qin F. Qian C. Sun J. Synthesis  2003,  1241 
• 6 Olah GA. Iyer PS. Surya Prakash GK. Synthesis  1986,  513 
• 7 Olah GA. Kaspi J. Bukala J. J. Org. Chem.  1977,  42:  4187 
• 8 Olah GA. Malhotra R. Narang SC. Olah JA. Synthesis  1978,  672 
• 9 Olah GA. Narang SC. Synthesis  1978,  690 
• 10 Olah GA. Narang SC. Meidar D. Salem GF. Synthesis  1981,  282 
• 11a Wolf JF. Rathman TL. Sleevi MC. Campbell JA. Greenwood TD. J. Med. Chem.  1990,  33:  161 
• 11b Padia JK. Field M. Hinton J. Meecham K. Pablo J. Pinnock R. Roth BD. Singh L. Suman-Chauhan N. Trivedi BK. Webdale L. J. Med. Chem.  1998,  41:  1042 
• 11c Khilil MA. Soliman R. Farghaly AM. Bekhit AA. Arch. Pharm. (Weinhem, Ger.)  1994,  32:  27 
• 12 Cohen E. Klarberg B. Vaughan JR. J. Am. Chem. Soc.  1960,  82:  2731 
• 13a Koepfly JB. Mead JF. Brockman JA. J. Am. Chem. Soc.  1947,  69:  1837 
• 13b Ablondi F. Gordon S. Morton J. Williams JH. J. Org. Chem.  1952,  17:  14 
• 13c Kobayashi S. Ueno M. Suzuki R. Ishitani H. Tetrahedron Lett.  1999,  40:  2175 
• 14 Jang CS. Fu FY. Wang CY. Huang KC. Lu G. Thou TC. Science (Washington, D.C.)  1946,  103:  59 
• 15 Rama Rao VVVNS. Reddy GV. Maitraie D. Ravi Kanth S. Yadla R. Narsaiah B. Shanthan Roa P. Tetrahedron  2004,  60:  12231 
• 16a Allias A, and Meier J. inventors;  Fr 1520743.  ; Chem. Abstr. , 71, 49975b
• 16b Keiichi K, Atsushi N, Mashashi H, Tamotsu M, Hiroto N, and Hisashi T. inventors; JP  o7258224.  ; Chem. Abstr. , 124, 176144t
• 16c Janiak S. inventors; Ger. Offen.  1908097.  ; Chem. Abstr. , 71, 124484
• 16d Wang L. Xia J. Qin F. Qian C. Sun J. Synthesis  2003,  1241 
• 16e Lietz W. Matthies H. Acta Biol. Med. Ger.  1964,  13:  4-591  
• 16f Dabiri M. Salehi P. Mohammadi AA. Baghbanzadeh M. Kozehgiry G. J. Chem. Res., Synop.  2004,  570 

17

General Procedure: A mixture of isatoic anhydride (1.8 mmol) or anthranilic acid (1.8 mmol), triethyl orthoester (1.8 mmol), aromatic aniline (1.8 mmol), and a catalytic amount of Nafion-H was irradiated in a domestic microwave oven at 800 W in an open tube for 2-6 min. After completion of the reaction the reaction mixture was allowed to cool to ambient temperature, dissolved in EtOAc, and the catalyst was separated by filtration. The organic layer was dried with Na₂SO₄ and concentrated. The solid was passed through a silica gel column (n-hexane-CHCl₃, 1:1) to furnish the title compound in sufficiently pure form.