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Synthesis 2008(24): 3963-3966
DOI: 10.1055/s-0028-1083258
DOI: 10.1055/s-0028-1083258
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
An Efficient Synthesis of Thio- and Thiazoloquinazolinones by the Electrochemical Oxidation of Catechols in the Presence of 2-Mercapto-4(3H)-quinazolinone
Further Information
Received
29 July 2008
Publication Date:
01 December 2008 (online)
Publication History
Publication Date:
01 December 2008 (online)

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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Cohen E.Klarberg B.Vaughan JR. J. Am. Chem. Soc. 1960, 82: 2731 - 2
Wolf JF.Rathman TL.Sleevi MC.Campbell JA.Greenwood TD. J. Med. Chem. 1990, 33: 161 - 3
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 - 4
Lingaiah BV.Ezikiel G.Yakaiah T.Reddy GV.Rao PS. Synlett 2006, 2507 - 5
Connolly DJ.Guiry PJ. Synlett 2001, 1707 - 6
Mhaske SB.Argade NP. Tetrahedron 2006, 62: 9787 - 7
Abdel-Jalil RJ.Voelter W.Saeed M. Tetrahedron Lett. 2004, 45: 3475 - 8
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 - 9
Besson T.Guillard J.Rees CW. Tetrahedron Lett. 2000, 41: 1027 - 10
Sauter F.Frohlich J.Chowdhury AZMS.Hametner C. Monatsh. Chem. 1997, 128: 503 - 11
Bouillon I.Krchnak V. J. Comb. Chem. 2007, 9: 912 - 12
Dhami KS.Arora SS.Narang KS. J. Med. Chem. 1963, 6: 450 - 13
LeMahieu RA.Carson M.Welton AF.Baruth HW.Yaremko B. J. Med. Chem. 1983, 26: 107 - 14
McCarty JE. J. Org. Chem. 1962, 27: 2673 -
15a
Bose PK.Pathak KB. J. Indian Chem. Soc. 1934, 11: 463 -
15b
Kate L. J. Am. Chem. Soc. 1958, 76: 712 - 16
Papouchado L.Petrie G.Adams RN. J. Electroanal. Chem. 1972, 38: 389 - 17
Nematollahi D.Rafiee M.Samadi-Meybodi A. Electrochim. Acta 2004, 49: 2495