Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 24, Pages 12552-12561Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b02419
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- Scientific and Technological Research Council of Turkey (TUBITAK) [TBAG-112 T360]
- Turkish Academy of Sciences (TUBA)
- Middle East Technical University (METU)
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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.
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