Synthesis of Benzoxazolylthiomethyl and Benzthiazolylthiomethyl Quinazolin-4(3h)-ones

GRAPHICAL ABSTRACT Abstract o-Aminophenol (1a, X = O) or o-aminothiophenol (1b, X = S) was reacted with carbon disulfide in ethanol containing KOH under reflux to obtain 2-mercaptobenzoxazole (2a, X = O) and 2-mercaptobenzthiazole (2b, X = S), respectively. Condensation of 2a and 2b each with chloroacetic acid gave 2-(benzoxazol-2-ylthio)acetic acid (3a, X = O) and 2-(benzthiazol-2-ylthio)acetic acid (3b, X = S) respectively which with anthranilamide gave 2-((benzoxal-2-ylthio)methyl) quinazolin-4(3H)-one (5a, X = O) and 2-((benzthiazol-2-ylthio)methyl)quinazolin-4(3H)-one (5b, X = S) respectively. The products 5a,b could be prepared in three other routes involving the general sequences 6→2→5, 6→7→5 and 8→9→5.

[1]  M. Alam,et al.  Sulfur rich 2-mercaptobenzothiazole and 1,2,3-triazole conjugates as novel antitubercular agents. , 2014, European journal of medicinal chemistry.

[2]  P. Dubey,et al.  Synthesis of Novel 2-(4-Oxo-3,4- Dihydroquinazolin-2-Ylsulfinylmethyl)-3H-Quinazolin-4-One , 2012 .

[3]  Nagwa M. Abdel Gawad,et al.  Synthesis and antitumor activity of some 2, 3-disubstituted quinazolin-4(3H)-ones and 4, 6- disubstituted- 1, 2, 3, 4-tetrahydroquinazolin-2H-ones. , 2010, European journal of medicinal chemistry.

[4]  S. Ganguly,et al.  Synthesis and antiulcer activity of 2-[5-substituted-1-H-benzo(d) imidazol-2-yl sulfinyl]methyl-3-substituted quinazoline-4-(3H) ones , 2010 .

[5]  M. Al-Omar,et al.  Non-classical antifolates. Part 2: synthesis, biological evaluation, and molecular modeling study of some new 2,6-substituted-quinazolin-4-ones. , 2010, Bioorganic & medicinal chemistry.

[6]  T. Yakaiah,et al.  Synthesis of novel 4,6-disubstituted quinazoline derivatives, their anti-inflammatory and anti-cancer activity (cytotoxic) against U937 leukemia cell lines. , 2008, European journal of medicinal chemistry.

[7]  N. Keen,et al.  Synthesis and SAR of 1-acetanilide-4-aminopyrazole-substituted quinazolines: selective inhibitors of Aurora B kinase with potent anti-tumor activity. , 2008, Bioorganic & Medicinal Chemistry Letters.

[8]  S. Kini,et al.  Synthesis and evaluation of new quinazolone derivatives of nalidixic acid as potential antibacterial and antifungal agents. , 2006, European journal of medicinal chemistry.

[9]  Yuyang Jiang,et al.  Synthesis and in vitro antitumor activity of 4(3H)-quinazolinone derivatives with dithiocarbamate side chains. , 2005, Bioorganic & medicinal chemistry letters.

[10]  Yuefen Zhou,et al.  Novel parallel synthesis of N-(4-oxo-2-substituted-4H-quinazolin-3-yl)-substituted sulfonamides , 2004 .

[11]  B. Suresh,et al.  Synthesis of 2-substituted quinazolin-4(3H)-ones as a new class of anticancer agents , 2003 .

[12]  D. Sriram,et al.  Synthesis, antibacterial, antifungal and anti-HIV evaluation of Schiff and Mannich bases of isatin derivatives with 3-amino-2-methylmercapto quinazolin-4(3H)-one. , 1999, Pharmaceutica acta Helvetiae.

[13]  G. Otuk,et al.  Pharmacological studies on quaternized 4(3H)-quinazolinones. , 1992, Journal of pharmaceutical sciences.

[14]  Y. Yamada,et al.  Studies on 4(1H)-quinazolinones. 5. Synthesis and antiinflammatory activity of 4(1H)-quinazolinone derivatives. , 1985, Journal of medicinal chemistry.

[15]  I. Setnikar,et al.  1-aminoacyl-2,3-dihydro-4(1H)-quinazolinone derivatives with choleretic and antifibrillatory activity. , 1968, Journal of medicinal chemistry.

[16]  M. Chaurasia,et al.  Some 6,8-dibromo-S-substituted-2-mercapto-3-aryl(or alkyl)-4-quinazolones , 1968 .

[17]  A. Scriabine,et al.  Antihypertensive 2-amino-4(3H)-quinazolinones. , 1968, Journal of medicinal chemistry.

[18]  C. E. Boord,et al.  THE PREPARATION AND PROPERTIES OF 1-MERCAPTO-BENZOTHIAZOLE, ITS HOMOLOGS AND DERIVATIVES1,2 , 1923 .