Design of Pyrazolo-pyrrolo-pyrazines and Pyrazolo-pyrrolo-diazepines via AuCl3-Catalyzed and NaH-Supported Cyclization of N-Propargyl Pyrazoles

Date

2015-04-17

Author

Basceken, Sinan
Balcı, Metin

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A concise synthetic methodology for new heterocyclic scaffolds, such as pyrazolo-pyrrolo-pyrazine and pyrazolo-pyrrolo-diazepine skeletons, was developed. The key features of this method include (i) synthesis of pyrrole-derived alpha,beta-alkynyl ketones, (ii) introduction of various substituents into the alkyne functionality by Sonogashira cross-coupling, (iii) synthesis of pyrazole units by the reaction of alpha,beta-alkynyl compounds with hydrazine monohydrate, (iv) gold-catalyzed cyclization of pyrazoles with alkyne units, and (v) cyclization with NaH. Furthermore, this methodology allows various substituents to be introduced into all positions of the target compounds.

Subject Keywords

GOLD-CATALYZED CYCLIZATION, RING-SYSTEMS DIAZINES, REGIOSELECTIVE SYNTHESIS, ALKYNES, HYDROAMINATION, FUNCTIONALIZATION, TRANSANNULATION, DERIVATIVES, HYDRAZONES, NITROGEN

URI

https://hdl.handle.net/11511/51297

Journal

JOURNAL OF ORGANIC CHEMISTRY

DOI

https://doi.org/10.1021/acs.joc.5b00034

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

S. Basceken and M. Balcı, “Design of Pyrazolo-pyrrolo-pyrazines and Pyrazolo-pyrrolo-diazepines via AuCl3-Catalyzed and NaH-Supported Cyclization of N-Propargyl Pyrazoles,” JOURNAL OF ORGANIC CHEMISTRY, pp. 3806–3814, 2015, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/51297.