Download PDF
Synthesis 2012(8): 1237-1246  
DOI: 10.1055/s-0031-1289731
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Direct Sulfanylation of 4-Quinazolinone via C-OH Bond Activation: An Efficient Route to 2-Aryl-4-sulfanylquinazolines

Yiyuan Peng*a, Guanyinsheng Qiub, Qin Yanga, Jianjun Yuana, Zhihong Dengb
a Key Laboratory of Small Fuctional Organic Molecule, Ministry of Education and College of Life Science, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
Fax: +86(791)88120396; e-Mail: yypeng@jxnu.edu.cn; e-Mail: Yiyuanpeng@yahoo.com;
b Key Laboratory of Green Chemistry, Jiangxi Province and College of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
Further Information

Publication History

Received 3 January 2012
Publication Date:
01 March 2012 (online)

    Permissions and Reprints All articles of this category

Abstract

The direct sulfanylation of 2-aryl-4-quinazolinones with thiols via C-OH bond activation under mild conditions is described. The method affords the corresponding 2-aryl-4-sulfanylquinazolines in good to excellent yield.

Key words

nitrogen heterocycles - multicomponent reactions - sulfinylations - thiols - bond activation

    References

  • For examples, see:
  • 1a Deng YJ. Zhou XL. Desmoulin SK. Wu JM. Cherian C. Hou ZJ. Matherly LH. Gangjee A. J. Med. Chem.  2009,  52:  2940 
    Google Scholar
  • 1b Kabri Y. Gellis A. Vanelle P. Green Chem.  2009,  11:  201 
    Google Scholar
  • 1c Witt A. Bergman J. Curr. Org. Chem.  2003,  7:  659 
    Google Scholar
  • 1d Lau H. Ferlan JT. Brophy VH. Rosowsky A. Sibley CH. Antimicrob. Agents Chemother.  2001,  45:  187 
    Google Scholar
  • 1e Desai P. Naik B. Desai CM. Patel D. Asian J. Chem.  1998,  10:  615 
    Google Scholar
  • 1f Dempcy RO. Skibo EB. Biochemistry  1991,  30:  8480 
    Google Scholar
  • 1g Calvert AH. Jones TR. Dady PJ. Grzelakowskasztabert B. Paine RM. Taylor GA. Harrap KR. Eur. J. Cancer  1980,  16:  713 
    Google Scholar
  • 2a Chen K. Al Aowad AF. Adelstein SJ. Kassis AI. J. Med. Chem.  2007,  50:  663 
    Google Scholar
  • 2b Michael JP. Nat. Prod. Rep.  2003,  20:  476 
    Google Scholar
  • 2c Michael JP. Nat. Prod. Rep.  2002,  19:  742 
    Google Scholar
  • 2d Michael JP. Nat. Prod. Rep.  1999,  16:  697 
    Google Scholar
  • 2e Chan JH. Baccanari DP. Tansik RL. Boytos CM. Rudolph SK. Brown AD. Hong JS. Kuyper LF. Jones ML. J. Heterocycl. Chem.  1997,  34:  145 
    Google Scholar
  • For examples of 4-aminoquinazolines, see:
  • 3a Sirisoma N. Pervin A. Zhang H. Jiang SC. Willardsen JA. Anderson MB. Mather G. Pleiman CM. Kasibhatla S. Tseng B. Drewe J. Cai SX. J. Med. Chem.  2009,  52:  2341 
    Google Scholar
  • 3b Murai M. Sekiguchi K. Nishioka T. Miyoshi H. Biochemistry  2009,  48:  688. 
    Google Scholar
  • 3c Chappie TA. Humphrey JM. Allen MP. Estep KG. Fox CB. Lebel LA. Liras S. Marr ES. Menniti FS. Pandit J. Schmidt CJ. Tu MH. Williams RD. Yang FV. J. Med. Chem.  2007,  50:  182 
    Google Scholar
  • 3d Yang S. Liu G. Song BA. Jin LH. Hu DY. Zhang SM. Chin. J. Org. Chem.  2006,  26:  1429 ; Chem. Abstr. 2007, 147, 301104
    Google Scholar
  • 3e Kanuma K. Omodera K. Nishiguchi M. Funakoshi T. Chaki S. Semple G. Tran TA. Kramer B. Hsu D. Casper M. Thomsen B. Beeley N. Sekiguchi Y. Bioorg. Med. Chem. Lett.  2005,  15:  2565 
    Google Scholar
  • 3f Liu G. Song BA. Sang WJ. Yang S. Jin LH. Ding X. Chin. J. Org. Chem.  2004,  24:  1296 ; Chem. Abstr. 2004, 142, 134667
    Google Scholar
  • 3g Shreder KR. Wong MS. Nomanbhoy T. Leventhal PS. Fuller SR. Org. Lett.  2004,  6:  3715 
    Google Scholar
  • 3h Tobe M. Isobe Y. Tomizawa H. Nagasaki T. Takahashi H. Fukazawa T. Hayashi H. Bioorg. Med. Chem.  2003,  11:  383 
    Google Scholar
  • 3i Rewcastle GW. Denny WA. Bridges AJ. Zhou HR. Cody DR. McMichael A. Fry DW.
    J. Med. Chem.  1995,  38:  3482 
    Google Scholar
  • 3j Rachid Z. Brahimi F. Qiu QY. Williams C. Hartaley JM. Hartaley JA. Jean-Claude BJ. J. Med. Chem.  2007,  50:  2605 
    Google Scholar
  • 3k Gomtsyan A. Bayburt EK. Schmidt RG. Zheng GZ. Perner RJ. Didomenico S. Koenig JR. Turner S. Jinkerson T. Drizin I. Hannick SM. Macri BS. McDonald HA. Honore P. Wismer CT. Marsh KC. Wetter J. Stewar KD. Oie T. Jarvis MF. Surowy CS. Faltynek CR. Lee CH. J. Med. Chem.  2005,  48:  744 
    Google Scholar
  • For examples of 4-alkyl(aryl)thioquinazolines, see
  • 4a Liu G. Liu CP. Ji CN. Sun L. Wen QW. Chin. J. Org. Chem.  2008,  28:  525 ; Chem. Abstr. 2009, 150, 121577
    Google Scholar
  • 4b Ma Y. Liu F. Yan K. Song BA. Yang S. Hu DY. Jin LH. Xue W. Chin. J. Org. Chem.  2008,  28:  1268 ; Chem. Abstr. 2009, 150, 352066
    Google Scholar
  • 4c Xu GF. Song BA. Bhadury PS. Yang S. Zhang PQ. Jin LH. Xue W. Hu DY. Lu P. Bioorg. Med. Chem.  2007,  15:  3768 
    Google Scholar
  • 5a 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 
    Google Scholar
  • 5b Alexandre F.-R. Berecibar A. Wrigglesworth R. Besson T. Tetrahedron  2003,  59:  1413 
    Google Scholar
  • For examples, see:
  • 6a Zhang YD. Xu CL. Houghten RA. Yu YP. J. Comb. Chem.  2007,  9:  9 
    Google Scholar
  • 6b Wéber C. Bielik A. Szendrei GI. Greiner I. Tetrahedron Lett.  2002,  43:  2971 
    Google Scholar
  • 6c Nakamura H. Onagi S. Tetrahedron Lett.  2006,  47:  2539 
    Google Scholar
  • 6d Seijas JA. Vãsquez-Tato MP. Martinez MM. Tetrahedron Lett.  2000,  41:  2215 
    Google Scholar
  • 7a Wacharasindhu S. Bardhan S. Wan Z.-K. Tabei K. Mansour TS. J. Am. Chem. Soc.  2009,  131:  4174 
    Google Scholar
  • 7b Kang F.-A. Sui ZH. Murray WV. J. Am. Chem. Soc.  2008,  130:  11300 
    Google Scholar
  • 7c Wan ZK. Wacharasindhu S. Levins CG. Lin M. Tabei K. Mansour TS. J. Org. Chem.  2007,  72:  10194 
    Google Scholar
  • 7d Wan ZK. Wacharasindhu S. Binnun E. Mansour T. Org. Lett.  2006,  8:  2425 
    Google Scholar
  • Homogeneous cross-coupling reactions based on either copper(I) or palladium have been developed for aromatic thiother syntheses, see:
  • 8a Kondo T. Mitsudo T. Chem. Rev.  2000,  100:  3205 
    Google Scholar
  • 8b Baranano D. Mann G. Hartwig JF. Curr. Org. Chem.  1997,  1:  187 
    Google Scholar
  • 8c Fernandez-Rodriguez MA. Shen Q. Hartwig JF. J. Am. Chem. Soc.  2006,  12:  2180 
    Google Scholar
  • 8d Cai LS. Cuevas J. Peng YY. Pike VW. Tetrahedron Lett.  2006,  47:  4449 
    Google Scholar
  • 9 Peng YY. Zeng YY. Qiu GYS. Cai L. Pike VW. J. Heterocycl. Chem.  2010,  47:  1240 
    Google Scholar
  • 10 Peng YY. Wen YF. Mao XC. Qiu GYS. Tetrahedron Lett.  2009,  50:  2405 
    Google Scholar