Synthesis 2016; 48(09): 1253-1268
DOI: 10.1055/s-0035-1560413
review
© Georg Thieme Verlag Stuttgart · New York

Advanced Synthetic Strategies for Constructing Quinazolinone Scaffolds

Rajendra S. Rohokale
Department of Chemistry, Savitribai Phule Pune University (Formerly: University of Pune), Ganeshkhind, Pune-411007, India   Email: [email protected]
,
Umesh A. Kshirsagar*
Department of Chemistry, Savitribai Phule Pune University (Formerly: University of Pune), Ganeshkhind, Pune-411007, India   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 08 December 2015

Accepted after revision: 28 December 2015

Publication Date:
09 March 2016 (online)


Abstract

Quinazolinones are important heterocyclic scaffolds because of their broad spectrum of medicinal and pharmacological properties. The development of advanced synthetic methods to construct the quinazolinone motif is therefore an important aspect of synthetic chemistry. This review emphasises the recent developments in methodologies and advanced synthetic strategies for the quinazolinone core.

1 Introduction

2 Synthesis of 2-Substituted Quinazolinones

2.1 Oxidative Condensation/Cyclization

2.2 Acid-Catalyzed Condensation/Cyclization

2.3 Transition-Metal-Catalyzed C–N Bond Formation

2.4 Transition-Metal-Catalyzed Cyclocarbonylation

3 Synthesis of 3-Substituted Quinazolinones

3.1 Using a Coupling Agent

3.2 Oxidative Condensation/Cyclization

3.3 Transition-Metal-Catalyzed C–N Bond Formation

3.4 Transition-Metal-Catalyzed Cyclocarbonylation

4 Synthesis of 2,3-Disubstituted Quinazolinones

4.1 Dehydrative/Reductive Cyclization

4.2 Oxidative Condensation/Cyclization

4.3 Radical Cyclization

4.4 Transition-Metal-Catalyzed C–N Bond Formation

4.5 Transition-Metal-Catalyzed Cyclocarbonylation

4.6 Acid-Catalyzed Condensation/Cyclization

5 Conclusion

 
  • References

    • 1a Chan JH, Hong JS, Kuyper LF, Jones ML, Baccanari DP, Tansik RL, Boytos CM, Rudolph SK, Brown AD. J. Heterocycl. Chem. 1997; 34: 145
    • 1b Gackenheimer SL, Schaus JM, Gehlert DR. J. Pharmacol. Exp. Ther. 1996; 732: 113
    • 1c Dempcy RO, Skibo EB. Biochemistry 1991; 30: 8480
    • 1d Nordisk-Droge 18113. Patent NA. Nordisk Drogeand Kemi-Kalieforretning AIS; Netherlands: 1965

      Reviews on quinazolinone alkaloid:
    • 2a Michael JP. Nat. Prod. Rep. 2005; 22: 627
    • 2b Michael JP. Nat. Prod. Rep. 2004; 21: 650
    • 2c Michael JP. Nat. Prod. Rep. 2003; 20: 476
    • 2d Mhaske SB, Argade NP. Tetrahedron 2006; 62: 9787
    • 2e Connolly DJ, Cusack D, O’Sullivan TP, Guiry PJ. Tetrahedron 2005; 61: 10153
    • 2f He L, Li HJ. C, Wu XF. RSC Adv. 2014; 4: 12065
    • 2g Abdou IM, Al-Neyadi SS. Heterocycl. Commun. 2015; 21: 115
    • 2h Khan I, Ibrar A, Abbas N, Saeed A. Eur. J. Med. Chem. 2014; 76: 193
    • 2i Khan I, Ibrar A, Ahmed W, Saeed A. Eur. J. Med. Chem. 2015; 90: 124
    • 2j Kshirsagar UA. Org. Biomol. Chem. 2015; 13: 9336
  • 3 Inoue I, Oine T, Yamada Y, Tani J, lshida R, Ochiai T. US Patent 3966731, 1974
  • 4 Purcell JW, Davis J, Reddy M, Shamra M, Kimberly S, Vo H, Thomsen K, Bean P, Kuo WL, Ziyad S, Billig J, Feiler HS, Gray JW, Wood KW, Cases S. Clin. Cancer Res. 2010; 16: 566
  • 5 Koepfli JB, Brockman JA. Jr, Moffat J. J. Am. Chem. Soc. 1950; 72: 3323
    • 6a Jiao RH, Xu S, Liu JY, Ge HM, Ding H, Xu C, Zhu HL, Tan RX. Org. Lett. 2006; 8: 5709
    • 6b Malgesini B, Forte B, Borghi D, Quartieri F, Gennari C, Papeo G. Chem. Eur. J. 2009; 15: 7922
  • 7 Chang RS, Lotti VJ, Monaghan RL, Birnbaum J, Stapley EO, Goetz MA, Albers-Schönberg G, Patchett AA, Liesch JM, Hensens OD, Springer JP. Science 1985; 230 (4722): 177
  • 8 Cagir A, Jones SH, Gao R, Eisenhauer BM, Hecht SM. J. Am. Chem. Soc. 2003; 125: 13628
    • 9a Hart DJ. ARKIVOC 2010; (iv): 32
    • 9b D’yakonov AL, Telezhenetskaya MV. Chem. Nat. Compd. 1997; 33: 221
    • 9c Ma Z, Hano Y, Nomura T. Heterocycles 2005; 65: 2203
    • 9d Witt A, Bergman J. Curr. Org. Chem. 2003; 7: 659
    • 9e Padala SR, Padi PR, Thipireddy V. Heterocycles 2003; 60: 183
  • 10 Chen J, Wu D, He F, Liu M, Wu H, Ding J, Su W. Tetrahedron Lett. 2008; 49: 3814
  • 11 Zhou J, Fang J. J. Org. Chem. 2011; 76: 7730
  • 12 Watson AJ. A, Maxwell AC, Williams JM. J. Org. Biomol. Chem. 2012; 10: 240
  • 13 Zhao D, Zhou Y.-R, Shen Q, Li J.-X. RSC Adv. 2014; 4: 6486
  • 14 Sharif MJ, Langer OP, Beller M, Wu X.-F. RSC Adv. 2014; 4: 8
  • 15 Ge W, Zhua X, Wei Y. RSC Adv. 2013; 3: 10817
  • 16 Qiu D, Wang Y, Lu D, Zhou L, Zeng Q. Monatsh. Chem. 2015; 146: 1343
  • 17 Siddiki SM. A. H, Kon K, Touchy AS, Shimizu K.-I. Catal. Sci. Technol. 2014; 4: 1716
  • 18 Zhang Z, Wang M, Zhang C, Zhang Z, Lu J, Wang F. Chem. Commun. 2015; 51: 9205
  • 19 Hikawa H, Ino Y, Suzuki H, Yokoyama Y. J. Org. Chem. 2012; 77: 7046
  • 20 Romero AH, Salazar J, Lopez SE. Synthesis 2013; 45: 2043
  • 21 Zhu Y.-P, Fei Z, Liu M.-C, Jia F.-C, Wu A.-X. Org. Lett. 2013; 15: 378
  • 22 Zhao D, Wang T, Li J.-X. Chem. Commun. 2014; 50: 6471
  • 23 Yang X, Cheng G, Shen J, Kuai C, Cui X. Org. Chem. Front. 2015; 2: 366
  • 24 Huang C, Fu Y, Fu H, Jiang Y, Zhao Y. Chem. Commun. 2008; 6333
  • 25 Liu X, Fu H, Jiang Y, Zhao Y. Angew. Chem. Int. Ed. 2009; 48: 348
  • 26 Yang D, Fu H, Hu L, Jiang Y, Zhao Y. J. Comb. Chem. 2009; 11: 653
  • 27 Xu W, Jin Y, Liu H, Jiang Y, Fu H. Org. Lett. 2011; 13: 1274
  • 28 Xu W, Fu H. J. Org. Chem. 2011; 76: 3846
  • 29 Wang L.-X, Xiang J.-F, Tang Y.-L. Eur. J. Org. Chem. 2014; 2682
  • 30 Hu B.-Q, Wang L.-X, Xiang J.-F, Yang L, Tang Y.-L. Chin. Chem. Lett. 2015; 26: 369
  • 31 Chai H, Li J, Yang L, Lu H, Qi Z, Shi D. RSC Adv. 2014; 4: 44811
  • 32 Ma B, Wang Y, Peng J, Zhu Q. J. Org. Chem. 2011; 76: 6362
    • 33a Wu X.-F, He L, Neumann H, Beller M. Chem. Eur. J. 2013; 19: 12635
    • 33b Li H, He L, Neumann H, Beller M, Wu X.-F. Green Chem. 2014; 16: 1336
  • 34 Jiang X, Tang T, Wang J.-M, Chen Z, Zhu Y.-M, Ji S.-J. J. Org. Chem. 2014; 79: 5082
  • 35 Xiao Z, Yang MG, Li P, Carter PH. Org. Lett. 2009; 11: 1421
  • 36 Punthasee P, Vanitcha A, Wacharasindhu S. Tetrahedron Lett. 2010; 51: 1713
  • 37 Bao Y, Yan Y, Xu K, Su J, Zha Z, Wang Z. J. Org. Chem. 2015; 80: 4736
  • 38 Yan Y, Xu Y, Niu B, Xie H, Liu Y. J. Org. Chem. 2015; 80: 5581
  • 39 Sreeramamurthy K, Ashok E, Mahendar V, Santoshkumar G, Das P. Synlett 2010; 721
  • 40 He L, Li H, Neumann H, Beller M, Wu X.-F. Angew. Chem. Int. Ed. 2014; 53: 1420
  • 41 He L, Sharif M, Neumann H, Beller M, Wu X.-F. Green Chem 2014; 16: 3763
  • 42 Kshirsagar UA, Mhaske SB, Argade NP. Tetrahedron Lett. 2007; 48: 3243
  • 43 Kostakis IK, Elomri A, Seguin E, Iannelli M, Besson T. Tetrahedron Lett. 2007; 48: 6609
  • 44 Tseng M.-C, Lai C.-Y, Chu Y.-W, Chu Y.-H. Chem. Commun. 2009; 445
  • 45 Tseng M.-C, Yang H.-Y, Chu Y.-H. Org. Biomol. Chem. 2010; 8: 419
  • 46 Liu J.-F, Ye P, Sprague K, Sargent K, Yohannes D, Baldino CM, Wilson CJ, Ng S.-C. Org. Lett. 2005; 7: 3363
  • 47 Liu J.-F, Ye P, Zhang B, Bi G, Sargent K, Yu L, Yohannes D, Baldino CM. J. Org. Chem. 2005; 70: 6339
  • 48 Liu J.-F, Kaselj M, Isome Y, Chapnick J, Zhang B, Bi G, Yohannes D, Yu L, Baldino CM. J. Org. Chem. 2005; 70: 10488
  • 49 Zhang W, Williams JP, Lu Y, Nagashima T, Chu Q. Tetrahedron Lett. 2007; 48: 563
  • 50 Zhichkin P, Kesicki E, Treiberg J, Bourdon L, Ronsheim M, Ooi HC, White S, Judkins A, Fairfax D. Org. Lett. 2007; 9: 1415
    • 51a Zhang C, De C K, Mal R, Seidel D. J. Am. Chem. Soc. 2008; 130: 416
    • 51b Dieckmann A, Richers MT, Platonova AY, Zhang C, Seidel D, Houk KN. J. Org. Chem. 2013; 78: 4132
    • 51c Richers MT, Zhao C, Seidel D. Beilstein J. Org. Chem. 2013; 9: 1194
  • 52 Jeong JU, Chen X, Rahman A, Yamashita DS, Luengo JI. Org. Lett. 2004; 6: 1013
  • 53 Lygin AV, De Meijere A. Org. Lett. 2009; 11: 389
  • 54 Wang H, Cao X, Xiao F, Liu S, Deng G.-J. Org. Lett. 2013; 15: 4900
  • 55 Wang Y.-F, Zhang F.-L, Chiba S. Org. Lett. 2013; 15: 2842
  • 56 Zhang F.-L, Wang Y.-F, Chiba S. Org. Biomol. Chem. 2013; 11: 6003
    • 57a Beaume A, Courillon C, Derat E, Malacria M. Chem. Eur. J. 2008; 14: 1238
    • 57b Larraufie M.-H, Courillon C, Ollivier C, Lacote E, Malacria M, Fensterbank L. J. Am. Chem. Soc. 2010; 132: 4381
  • 58 Xu L, Jiang Y, Ma D. Org. Lett. 2012; 14: 1150
  • 59 Zhou J, Fu L, Lv M, Liu J, Pei D, Ding K. Synthesis 2008; 24: 3974
  • 60 Li B, Samp L, Sagal J, Hayward CM, Yang C, Zhang Z. J. Org. Chem. 2013; 78: 1273
  • 61 Kshirsagar UA, Argade NP. Org. Lett. 2010; 12: 3716
    • 62a Zheng Z, Alper H. Org. Lett. 2008; 10: 829
    • 62b Sadig JR. R, Foster R, Wakenhut F, Willis MC. J. Org. Chem. 2012; 77: 9473
  • 63 Liang D, He Y, Zhu Q. Org. Lett. 2014; 16: 2748
  • 64 Chen J, Natte K, Spannenberg A, Neumann H, Langer P, Beller M, Wu X.-F. Angew. Chem. Int. Ed. 2014; 53: 7579
  • 65 Li H, Li W, Spannenberg A, Baumann W, Neumann H, Beller M, Wu X.-F. Chem. Eur. J. 2014; 20: 8541
  • 66 Shen C, Man NY. T, Stewart S, Wu X.-F. Org. Biomol. Chem. 2015; 13: 4422
  • 67 Wang H, Jiao S, Chen K, Zhang X, Zhao L, Liu D, Zhou Y, Liu H. Beilstein J. Org. Chem. 2015; 11: 416
  • 68 Li Z, Dong J, Chen X, Li Q, Zhou Z, Yin S. J. Org. Chem. 2015; 80: 9392
    • 69a Laclef S, Harari M, Godeau J, Schmitz-Afonso I, Bischoff L, Hoarau C, Levacher V, Fruit C, Besson T. Org. Lett. 2015; 17: 1700
    • 69b Godeau J, Harari M, Laclef S, Deau E, Fruit C, Besson T. Eur. J. Org. Chem. 2015; 7705