title: Design of pyrazolo-pyrrolo-pyrazines and pyrazolo-pyrrolo-diazepines via AuCl₃-catalyzed and NaH-supported cyclization of N-propargyl pyrazoles.
abstract: 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 α,β-alkynyl ketones, (ii) introduction of various substituents into the alkyne functionality by Sonogashira cross-coupling, (iii) synthesis of pyrazole units by the reaction of α,β-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.
authors: †Department of Chemistry, Middle East Technical University, 06800 Ankara, Turkey.|‡Department of Chemistry, Hitit University, 19030 Corum, Turkey.
authors: Sinan
authors: S
authors: Basceken
authors: †Department of Chemistry, Middle East Technical University, 06800 Ankara, Turkey.
authors: Metin
authors: M
authors: Balci
mesh_terms: D001381:Azepines / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D017612:Gold Compounds / Q000737:chemistry*; D015394:Molecular Structure; D009019:Morphinans / Q000737:chemistry*; D011719:Pyrazines / Q000138:chemical synthesis* / Q000737:chemistry*; D011720:Pyrazoles / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*
chemical_list: D001381:Azepines; D017612:Gold Compounds; D009019:Morphinans; C440369:N-propargyl; D011719:Pyrazines; D011720:Pyrazoles; D011758:Pyrroles; C038016:gold chloride