An Efficient Synthesis of Thio-
and Thiazoloquinazolinones by the Electrochemical Oxidation
of Catechols in the Presence of 2-Mercapto-4(3H)-quinazolinone

Ali Reza Fakhari; Kobra Hasheminasab; Hamid Ahmar; Abdolali Alizadeh

doi:10.1055/s-0028-1083258

PAPER

An Efficient Synthesis of Thio- and Thiazoloquinazolinones by the Electrochemical Oxidation of Catechols in the Presence of 2-Mercapto-4(3H)-quinazolinone

Ali Reza Fakhari*^a, Kobra Hasheminasab^a, Hamid Ahmar^a, Abdolali Alizadeh^b
^a Department of Chemistry, Faculty of Sciences, Shahid Beheshti University G. C., P.O. Box 19396-4716, Tehran, Iran
Fax: +98(21)22431683; e-Mail: a-zavareh@sbu.ac.ir;
^b Department of Chemistry, Tarbiat Modares University, Tehran 18716, Iran

Abstract

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Abstract

Thio- and thiazoloquinazolinones were synthesized efficiently by the anodic oxidation of catechols in the presence of 2-mercapto-4(3H)-quinazolinone in aqueous solution. 4-Methylcatechol and 3-methoxycatechol convert into thioquinazolinones via an EC (E: electron transfer, C: chemical reaction) pathway. Catechol, 3-methylcatechol, and 3,4-dihydroxybenzoic acid convert into thiazoloquinazolinones via an ECEC pathway.

Key words

electrochemical synthesis - phenols - thiols - heterocycles - decarboxylation

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References

<A NAME="RZ17508SS-1">1</A> Cohen E. Klarberg B. Vaughan JR. J. Am. Chem. Soc. 1960, 82: 2731

<A NAME="RZ17508SS-2">2</A> Wolf JF. Rathman TL. Sleevi MC. Campbell JA. Greenwood TD. J. Med. Chem. 1990, 33: 161

<A NAME="RZ17508SS-3">3</A> 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

<A NAME="RZ17508SS-4">4</A> Lingaiah BV. Ezikiel G. Yakaiah T. Reddy GV. Rao PS. Synlett 2006, 2507

<A NAME="RZ17508SS-5">5</A> Connolly DJ. Guiry PJ. Synlett 2001, 1707

<A NAME="RZ17508SS-6">6</A> Mhaske SB. Argade NP. Tetrahedron 2006, 62: 9787

<A NAME="RZ17508SS-7">7</A> Abdel-Jalil RJ. Voelter W. Saeed M. Tetrahedron Lett. 2004, 45: 3475

<A NAME="RZ17508SS-8">8</A> Rewcastle GW. Palmer BD. Bridges AJ. Showalter HDH. Sun L. Nelson J. McMichael A. Kraker AJ. Fry DW. Denny WA. J. Med. Chem. 1996, 39: 918

<A NAME="RZ17508SS-9">9</A> Besson T. Guillard J. Rees CW. Tetrahedron Lett. 2000, 41: 1027

<A NAME="RZ17508SS-10">10</A> Sauter F. Frohlich J. Chowdhury AZMS. Hametner C. Monatsh. Chem. 1997, 128: 503

<A NAME="RZ17508SS-11">11</A> Bouillon I. Krchnak V. J. Comb. Chem. 2007, 9: 912

<A NAME="RZ17508SS-12">12</A> Dhami KS. Arora SS. Narang KS. J. Med. Chem. 1963, 6: 450

<A NAME="RZ17508SS-13">13</A> LeMahieu RA. Carson M. Welton AF. Baruth HW. Yaremko B. J. Med. Chem. 1983, 26: 107

<A NAME="RZ17508SS-14">14</A> McCarty JE. J. Org. Chem. 1962, 27: 2673

<A NAME="RZ17508SS-15A">15a</A> Bose PK. Pathak KB. J. Indian Chem. Soc. 1934, 11: 463

<A NAME="RZ17508SS-15B">15b</A> Kate L. J. Am. Chem. Soc. 1958, 76: 712

<A NAME="RZ17508SS-16">16</A> Papouchado L. Petrie G. Adams RN. J. Electroanal. Chem. 1972, 38: 389

<A NAME="RZ17508SS-17">17</A> Nematollahi D. Rafiee M. Samadi-Meybodi A. Electrochim. Acta 2004, 49: 2495