Synthesis 2019; 51(17): 3287-3294
DOI: 10.1055/s-0037-1610711
paper
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed C12-Selective Direct Arylation of [1,2-c]Quinazolin-6(5H)-ones

Antonio Arcadi
a   Dipartimento di Scienze Fisiche e Chimiche, Università di L’Aquila, Via Vetoio, 67010 Coppito (AQ), Italy
,
Sandro Cacchi
b   Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy   Email: antonella.goggiamani@uniroma1.it   Email: antonia.iazzetti@uniroma1.it
,
Giancarlo Fabrizi
b   Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy   Email: antonella.goggiamani@uniroma1.it   Email: antonia.iazzetti@uniroma1.it
,
Andrea Fochetti
b   Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy   Email: antonella.goggiamani@uniroma1.it   Email: antonia.iazzetti@uniroma1.it
,
Francesca Ghirga
c   Center for Life Nano Science@Sapienza, Istituto Italiano di Tecnologia, Viale Regina Elena 291, 00161 Rome, Italy
,
Antonella Goggiamani*
b   Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy   Email: antonella.goggiamani@uniroma1.it   Email: antonia.iazzetti@uniroma1.it
,
b   Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy   Email: antonella.goggiamani@uniroma1.it   Email: antonia.iazzetti@uniroma1.it
,
Fabio Marinelli
a   Dipartimento di Scienze Fisiche e Chimiche, Università di L’Aquila, Via Vetoio, 67010 Coppito (AQ), Italy
› Author Affiliations
We gratefully acknowledge the University of l’Aquila and the Sapienza, University of Rome, for financial support.
Further Information

Publication History

Received: 05 March 2019

Accepted after revision: 13 April 2019

Publication Date:
07 May 2019 (online)


Abstract

A straightforward approach to the synthesis of the challenging 12-arylindolo[1,2-c]quinazolin-6(5H)-ones through the palladium-catalyzed direct arylation of N-benzyl and NH-free [1,2-c]quinazolin-6(5H)-ones with aryl halides is described.

Supporting Information

 
  • References

  • 1 Ren Z.-L, Kong H.-H, Lu W.-T, Sun M, Ding M.-W. Tetrahedron 2018; 74: 184 ; and references cited therein
  • 2 Honda G, Tabata M, Tsuda M. Planta Med. 1979; 37: 172
  • 3 Krivogorsky B, Nelson AC, Douglas KA, Grundt P. Bioorg. Med. Chem. Lett. 2013; 23: 1032
  • 4 Sharma VM, Prasanna P, Seshu KV. A, Renuka B, Rao CV. L, Kumar GS, Narasimhulu CP, Babu PA, Puranik RC, Subramanyam D, Venkateswarlu A, Rajagopal S, Kumar KB. S, Rao CS, Mamidi DS, Deevi NV. S. R, Ajaykumar R, Rajagopalan R. Bioorg. Med. Chem. Lett. 2002; 12: 2303
  • 5 Hwang J.-M, Oh T, Kaneko T, Upton AM, Franzblau SG, Ma Z, Cho S.-N, Kim P. J. Nat. Prod. 2013; 76: 354
  • 6 Arcadi A, Cacchi S, Fabrizi G, Ghirga F, Goggiamani A, Iazzetti A, Marinelli F. Synthesis 2018; 50: 1133
    • 7a Ponpandian T, Muthusubramanian S. Tetrahedon Lett. 2012; 53: 4248
    • 7b Gerfaud T, Wei H.-L, Zhu J. Org. Lett. 2011; 13: 6175
    • 7c Olivella S, Solé A, Jiménez Ó, Bosch MP, Guerrero A. J. Am. Chem. Soc. 2005; 127: 2620
    • 7d Cordaro JG, Bergman RG. J. Am. Chem. Soc. 2004; 126: 16912

      For recent reviews on the C–H arylation of arenes, see:
    • 8a Seregin IV, Gevorgyan V. Chem. Soc. Rev. 2007; 36: 1173
    • 8b Alberico D, Scott ME, Lautens M. Chem. Rev. 2007; 107: 174
    • 8c Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
    • 8d Ackermann L. Angew. Chem. Int. Ed. 2009; 48: 9792
    • 8e Bellina F, Rossi R. Tetrahedron 2009; 65: 10269
    • 8f Lei A, Liu W, Liu C, Chen M. Dalton Trans. 2010; 39: 10352
    • 8g Wencel-Delord J, Drçge T, Liu F, Glorius F. Chem. Soc. Rev. 2011; 40: 4740
    • 8h Ackermann L. Chem. Rev. 2011; 111: 1315
    • 8i Hirano K, Miura M. Synlett 2011; 294
    • 8j Neufeldt SR, Sanford MS. Acc. Chem. Res. 2012; 45: 936
    • 8k Glorius F. Angew. Chem. Int. Ed. 2012; 51: 10236
    • 8l Yang Y, Lan J, You J. Chem. Rev. 2017; 117: 8787
    • 9a Ohta A, Akita Y, Ohkuwa T, Chiba M, Fukunaga R, Miyafuji A, Nakata T, Tani N, Aoyagi Y. Heterocycles 1990; 31: 1951
    • 9b Lane BS, Sames D. Org. Lett. 2004; 6: 2897
    • 9c Toure BB, Lane BS, Sames D. Org. Lett. 2006; 8: 1979
    • 9d Djakovitch L, Dufaud V, Zaidi R. Adv. Synth. Catal. 2006; 348: 715
    • 9e Lebrasseur N, Larrosa I. J. Am. Chem. Soc. 2008; 130: 2926
    • 9f Cacchi S, Fabrizi G, Goggiamani A, Iazzetti A. Org. Biomol. Chem. 2012; 10: 9142
    • 9g Dao-Huy T, Haider M, Glatz F, Schnürch M, Mihovilovic MD. Eur. J. Org. Chem. 2014; 8119
    • 9h Walsh PJ. Org. Lett. 2018; 20: 2522
    • 9i Lavrard H, Popowycz F. Synthesis 2018; 50: 998
    • 9j He G, Xue XS, Chen G. Org. Lett. 2018; 20: 1684
  • 10 Wang X, Gribkov DV, Sames D. J. Org. Chem. 2007; 72: 1476
  • 11 Jeffery T. Tetrahedron 1996; 52: 10113
  • 12 Forbes IT, Johnson CN, Thompson M. J. Chem. Soc., Perkin Trans. 1 1992; 275
  • 13 Arcadi A, Cacchi S, Fabrizi G, Marinelli F, Parisi LM. Heterocycles 2004; 64: 475
  • 15 Arcadi A, Cacchi S, Fabrizi G, Ghirga F, Goggiamani A, Iazzetti A, Marinelli F. Beilstein J. Org. Chem. 2018; 14: 2411