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Synthesis 2013; 45(14): 1965-1974
DOI: 10.1055/s-0033-1338936
paper
© Georg Thieme Verlag Stuttgart · New York

A Practical, Ligand-Free, Palladium-Catalyzed Isocyanide Insertion Reaction for the Construction of Novel Ring-Fused Quinazolinones

Fei Ji
Chemical Engineering College, Nanjing University of Science and Technology, Nanjing 210094, P. R. of China   Fax: +86(25)84315030   Email: c.cai@mail.njust.edu.cn
,
Mei-fang Lv
Chemical Engineering College, Nanjing University of Science and Technology, Nanjing 210094, P. R. of China   Fax: +86(25)84315030   Email: c.cai@mail.njust.edu.cn
,
Wen-bin Yi
Chemical Engineering College, Nanjing University of Science and Technology, Nanjing 210094, P. R. of China   Fax: +86(25)84315030   Email: c.cai@mail.njust.edu.cn
,
Chun Cai*
Chemical Engineering College, Nanjing University of Science and Technology, Nanjing 210094, P. R. of China   Fax: +86(25)84315030   Email: c.cai@mail.njust.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 04 March 2013

Accepted after revision: 17 April 2013

Publication Date:
14 May 2013 (online)

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Abstract

A high-yielding, ligand-free, palladium-catalyzed isocyanide insertion reaction for the synthesis of phthalazino[1,2-b]quinazolinones from the readily obtainable quinazolinones has been developed. Easily handled and relatively low-cost palladium(II) acetate was used as the catalyst, without an additional ligand. Preparation of the quinazolinones involved the cascade reaction of isatoic anhydrides, phenylhydrazines and 2-bromobenzaldehyde catalyzed by p-toluenesulfonic acid in one pot. This novel protocol may be applicable for the synthesis of other important ring-fused heterocyclic compounds.

Key words

ligand-free - palladium catalysis - isocyanide insertion reaction - ring-fused quinazolinones - depropargylation

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
  • Supporting Information

Primary Data

    for this article are available online at http­://www.thieme-connect.com/ejournals/toc/synthesis and can be cited using the following DOI: 10.4125/pd0046th
  • Primary Data
 

  • References

    • 1a Lygin AV, de Meijere A. Angew. Chem. Int. Ed. 2010; 49: 9094
      Crossref
    • 1b Yue T, Wang M.-X, Wang D.-X, Masson G, Zhu J. J. Org. Chem. 2009; 74: 8396
      Crossref
    • 1c Mihara H, Xu Y, Shepherd NE, Matsunaga S, Shibasaki M. J. Am. Chem. Soc. 2009; 131: 8384
      CrossrefPubMed
    • 1d Scheffelaar R, Paravidino M, Muilwijk D, Lutz M, Spek AL, De Kanter FJ. J, Orru RV. A, Ruijter E. Org. Lett. 2009; 11: 125
      Crossref
    • 1e Pirali T, Tron GC, Masson G, Zhu J. Org. Lett. 2007; 9: 5275
      Crossref
    • 1f Wang S.-X, Wang M.-X, Wang D.-X, Zhu J. Org. Lett. 2007; 9: 3615
      Crossref
    • 1g Pirali T, Tron GC, Zhu J. Org. Lett. 2006; 8: 4145
      CrossrefPubMed
    • 1h Janvier P, Bois-Choussy M, Bienaym H, Zhu J. Angew. Chem. Int. Ed. 2003; 42: 811
      CrossrefPubMed
    • 2a Ishiyama T, Oh-e T, Miyaura N, Suzuki A. Tetrahedron Lett. 1992; 33: 4465
      Crossref
    • 2b Saluste CG, Whitby RJ, Furber M. Tetrahedron Lett. 2001; 42: 6191
      Crossref
    • 2c Whitby RJ, Saluste CG, Furber M. Org. Biomol. Chem. 2004; 2: 1974
      Crossref
    • 2d Wang Y, Wang H, Peng J, Zhu Q. Org. Lett. 2011; 13: 4604
      CrossrefPubMed
  • 3 Saluste CG, Whitby RJ, Furber M. Angew. Chem. Int. Ed. 2000; 39: 4156
    CrossrefPubMed
    • 4a Ito Y. J. Synth. Org. Chem., Jpn. 2010; 68: 1239
      Crossref
    • 4b Nakamura I, Yamamoto Y. Chem. Rev. 2004; 104: 2127
    • 4c Patil NT, Yamamoto Y. Chem. Rev. 2008; 108: 3395
      CrossrefPubMed
    • 5a Wang Y, Zhu Q. Adv. Synth. Catal. 2012; 354: 1902
      Crossref
    • 5b Tyagi V, Khan S, Giri A, Gauniyal HM, Sridhar B, Chauhan PM. S. Org. Lett. 2012; 14: 3126
      CrossrefPubMed
    • 5c Qiu G, He Y, Wu J. Chem. Commun. 2012; 48: 3836
      Crossref
    • 5d Vlaar T, Ruijter E, Znabet A, Janssen E, De Kanter FJ. J, Maes BU. W, Orru RV. A. Org. Lett. 2011; 13: 6496
      CrossrefPubMed
    • 5e Tobisu M, Imoto S, Ito S, Chatani N. J. Org. Chem. 2010; 75: 4835
      Crossref
    • 5f Qiu G, Liu G, Pu S, Wu J. Chem. Commun. 2012; 48: 2903
      CrossrefPubMed
    • 5g Nanjo T, Tsukano C, Takemoto Y. Org. Lett. 2012; 14: 4270
      Crossref
    • 5h Liu B, Li Y, Jiang H, Yin M, Huang H. Adv. Synth. Catal. 2012; 354: 2288
      Crossref
    • 5i Hu Z, Liang D, Zhao J, Huang J, Zhu Q. Chem. Commun. 2012; 48: 7371
      CrossrefPubMed
    • 5j Zhu C, Xie W, Falck JR. Chem. Eur. J. 2011; 17: 12591
      CrossrefPubMed
    • 5k Van Baelen G, Kuijer S, Rýček L, Sergeyev S, Janssen E, De Kanter FJ. J, Maes BU. W, Ruijter E, Orru RV. A. Chem. Eur. J. 2011; 17: 15039
      Crossref
    • 5l Cai Q, Zhou F, Xu T, Fu L, Ding K. Org. Lett. 2011; 13: 340
      CrossrefPubMed
    • 5m Tobisu M, Kitajima A, Yoshioka S, Hyodo I, Oshita M, Chatani N. J. Am. Chem. Soc. 2007; 129: 11431
      Crossref
    • 5n Komeyama K, Sasayama D, Kawabata T, Takehira K, Takaki K. Chem. Commun. 2005; 634
    • 5o Boissarie PJ, Hamilton ZE, Lang SJ, Murphy A, Suckling CJ. Org. Lett. 2011; 13: 6256
      CrossrefPubMed
    • 5p Peng J, Liu L, Hu Z, Huang J, Zhu Q. Chem. Commun. 2012; 48: 3772
      Crossref
    • 6a Chiou W.-F, Chen C.-F. Eur. J. Pharmacol. 2002; 446: 151
      Crossref
    • 6b Asahina Y, Kashiwaki K. J. Pharm. Soc. Jpn. 1915; 405: 1293 ; Chem. Abstr. 1916, 10, 607
    • 6c Ma Z.-Z, Hano Y, Nomura T, Chen Y.-J. Heterocycles 1997; 46: 541
      Crossref
    • 6d Sen AK, Mahato SB, Dutta NL. Tetrahedron Lett. 1974; 609
    • 6e Amin AH, Mehta DR. Nature (London) 1959; 183: 1317
      Crossref
    • 7a Mhaske SB, Argade NP. Tetrahedron 2006; 62: 9787
      Crossref
    • 7b Zhou J, Fang J. J. Org. Chem. 2011; 76: 7730
      CrossrefPubMed
    • 7c Granger BA, Kaneda K, Martin SF. Org. Lett. 2011; 13: 4542
      Crossref
  • 8 Ukhin LYu, Kuz’mina LG, Gribanova TN, Belousova LV, Orlova ZhI. Russ. Chem. Bull. 2008; 57: 2340
    Crossref
    • 9a Ghelardoni M, Pestellini V. Ann. Chim. (Rome) 1974; 64: 445
    • 9b Siva Kumar K, Mahesh Kumar P, Sreenivasa Rao V, Jafar AA, Meda CL. T, Kapavarapu R, Parsa KV. L, Pal M. Org. Biomol. Chem. 2012; 10: 3098
      Crossref
    • 9c Guggenheim K, Toru GH, Kurth MJ. Org. Lett. 2012; 14: 3732
      Crossref
    • 9d Peet NP, Sunder S, Brawn WH. J. Org. Chem. 1976; 41: 2728
      Crossref
    • 10a Wang X.-S, Yang K, Zhou J, Tu S.-J. J. Comb. Chem. 2010; 12: 417
      CrossrefPubMed
    • 10b Patil NT, Lakshmi PG. V. V, Sridhar B, Patra S, Pal Bhadra M, Patra CR. Eur. J. Org. Chem. 2012; 1790
    • 11a Periasamy M, Sanjeevakumar N, Dalai M, Gurubrahamam R, Reddy PO. Org. Lett. 2012; 14: 2932
      CrossrefPubMed
    • 11b Lo VK, Wong M.-K, Che C.-M. Org. Lett. 2008; 10: 517
      CrossrefPubMed
    • 11c Pal M, Parasuraman K, Yeleswarapu KR. Org. Lett. 2003; 5: 349
      Crossref
    • 11d Earl RA, Peter K, Vollhardt C. Heterocycles 1982; 19: 265
      Crossref
    • 12a Fei X.-D, Ge Z.-Y, Tang T, Zhu Y.-M, Ji S.-J. J. Org. Chem. 2012; 77: 10321
      Crossref
    • 12b Miura T, Nishida Y, Morimoto M, Yamauchi M, Murakami M. Org. Lett. 2011; 13: 1429
      Crossref