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

2015-04-17
Basceken, Sinan
Balcı, Metin
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.

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, vol. 80, no. 8, pp. 3806–3814, 2015, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/51297.