Synthesis, Inhaltsverzeichnis Synthesis 2019; 51(15): 2936-2944DOI: 10.1055/s-0037-1612426 paper © Georg Thieme Verlag Stuttgart · New YorkIntramolecular 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› InstitutsangabenArtikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik 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. Key words Key wordsisocyanide - dialkyl acetylenedicarboxylate - 2-furancarboxylic acid - epoxypyrrolo[3,4-g]indazole - IMDA - [3+2] cycloaddition - oxabicyclo compounds Volltext Referenzen 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 3a Woodward RB. J. Am. Chem. Soc. 1940; 62: 1478 3b Li W.-DZ, Wei K. Org. Lett. 2004; 6: 1333 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 16a Alizadeh A, Rostamnia S, Zoreh N, Oskueyan Q. Synlett 2007; 1610 16b Alizadeh A, Oskueyan Q, Rostamnia S. Synthesis 2007; 2637 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 Zusatzmaterial Zusatzmaterial Supporting Information
