Synthesis 2019; 51(15): 2936-2944
DOI: 10.1055/s-0037-1612426
paper
© Georg Thieme Verlag Stuttgart · New York

Intramolecular Diels–Alder and [3+2] Cycloaddition Reactions in the One-Pot Synthesis of Epoxypyrrolo[3,4-g]indazoles

Abdolali Alizadeh*
a   Department of Chemistry, Tarbiat Modares University, P. O. Box 14115-175, Tehran, Iran   Email: aalizadeh@modares.ac.ir
,
Kaveh Amir Ashjaee Asalemi
a   Department of Chemistry, Tarbiat Modares University, P. O. Box 14115-175, Tehran, Iran   Email: aalizadeh@modares.ac.ir
,
Mohammadreza Halvagar
b   Department of Inorganic Chemistry, Chemistry and Chemical Engineering Research Center of Iran, P. O. Box 14335-186, Tehran, Iran
› Author Affiliations
We gratefully thank Tarbiat Modares University for financial support.
Further Information

Publication History

Received: 03 February 2019

Accepted after revision: 08 March 2019

Publication Date:
10 April 2019 (online)


Abstract

A one-pot approach for the synthesis of epoxypyrrolo[3,4-g]indazoles is presented. The first step was initiated by a three-component reaction of an isocyanide, a dialkyl acetylenedicarboxylate, and 2-furancarboxylic acid, and led to 1,3-dioxoepoxyisoindole, followed by the addition of hydrazonoyl chloride through a [3+2]-cycloaddition reaction in the second step. The key step in the formation of final compound involves a bicyclization strategy through intramolecular Diels–Alder­ (IMDA) reaction.

Supporting Information

 
  • References

  • 1 Saleem M, Ali MS, Hussain S, Jabbar A, Ashraf M, Lee YS. Nat. Prod. Rep. 2007; 24: 1142
  • 2 Schindler CS, Carreira EM. Chem. Soc. Rev. 2009; 38: 3222
    • 4a Shoji M, Yamaguchi J, Kakeya H, Osada H, Hayashi Y. Angew. Chem. Int. Ed. 2002; 41: 3192
    • 4b Shoji M, Imai H, Shiina I, Kakeya H, Osada H, Hayashi Y. J. Org. Chem. 2004; 69: 1548
  • 5 Chandler CL, Phillips AJ. Org. Lett. 2005; 7: 3493
  • 6 Kitamura M, Ihara Y, Uera K, Narasaka K. Bull. Chem. Soc. Jpn. 2006; 79: 1552
  • 7 Vogel P, Cossy J, Plumet J, Arjona O. Tetrahedron 1999; 55: 13521
    • 8a McCluskey A, Sim AT, Sakoff JA. J. Med. Chem. 2002; 45: 1151
    • 8b McCluskey A, Walkom C, Bowyer MC, Ackland SP, Gardiner E, Sakoff JA. Bioorg. Med. Chem. Lett. 2001; 11: 2941
  • 9 Huyen CT. T, Luyen BT. T, Khan GJ, Oanh HV, Hung TM, Li H.-J, Li P. Molecules 2018; 23: 1083
  • 10 Ciganek E. Org. React. 2004; 32: 1
    • 11a Juhl M, Tanner D. Chem. Soc. Rev. 2009; 38: 2983
    • 11b Heravi MM, Vavsari VF. RSC Adv. 2015; 5: 50890
  • 12 Liu L, Gao Y, Che C, Wu N, Wang DZ, Li C.-C, Yang Z. Chem. Commun. 2009; 662
  • 13 Liu G, Han J.-C, Li C.-C. Tetrahedron 2017; 73: 3629
  • 14 Miyashita M, Sasaki M, Hattori I, Sakai M, Tanino K. Science 2004; 305: 495
  • 15 Gao Q, Hao W.-J, Liu F, Tu S.-J, Wang S.-L, Li G, Jiang B. Chem. Commun. 2016; 52: 900
  • 17 CCDC 1900188 (6b and 6′b) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
  • 18 Alizadeh A, Rostamnia S, Zhu L.-G. Tetrahedron 2006; 62: 5641