Intramolecular Gold-Catalyzed and NaH-supported cyclization reactions of N-Propargyl indole derivatives with Pyrazole and Pyrrole rings: Synthesis of Pyrazolodiazepinoindole, Pyrazolopyrazinoindole, and Pyrrolopyrazinoindole

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2015-12-18

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Basceken, Sinan
Kaya, Serdal
Balci, Metin

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Gold-catalyzed and NaH-supported intramolecular cyclization of N-propargyl indole derivatives with pyrazole and pyrrole units attached to indole is described. An efficient route to the synthesis of pyrazolodiazepinoindole, pyrazolopyrazinoindole, and pyrrolopyrazinoindole has been established. First, N-propargyl 2-(1H-pyrazol-5-yl)-1H-indole and 2-(1H-pyrrol-2-yl)-1H-indole were synthesized. Introduction of various substituents into the alkyne functionality was accomplished by Sonogashira cross-coupling reaction. Gold-catalyzed cyclization- of pyratoles having a terminal alkyne afforded the 6-exo-dig cyclization:product. However, exclusive formation of 7-endo-dig-cyclization products was observed with internal alkynes. On the other hark; cyclization with NaH only resulted in the formation of 6-exo-dig cyclization products regardless of the substitution of the alkyne functionality. Allenic intermediates were postulated for this outcome.

Subject Keywords

3-Haloındoles;, Desıgn;, Enynes;, Potent

URI

https://hdl.handle.net/11511/28633

Journal

Journal Of Organıc Chemıstry

DOI

https://doi.org/10.1021/acs.joc.5b02419

Collections

Department of Chemistry, Article

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Citation Formats

S. Basceken, S. Kaya, and M. Balci, “Intramolecular Gold-Catalyzed and NaH-supported cyclization reactions of N-Propargyl indole derivatives with Pyrazole and Pyrrole rings: Synthesis of Pyrazolodiazepinoindole, Pyrazolopyrazinoindole, and Pyrrolopyrazinoindole,” Journal Of Organıc Chemıstry, pp. 12552–12561, 2015, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/28633.