Sequential Base-Promoted Annulation/Palladium-Catalyzed Domino 1,5-Enyne Arylation and Vinylation of α-Propargylaminohydrazones

Rossi, Elisabetta; Arcadi, Antonio; Abbiati, Giorgio; Attanasi, Orazio A.; Crescentini, Lucia De

doi:10.1002/1521-3773(20020415)41:8<1400::aid-anie1400>3.0.co;2-3

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2 Synthesis Of Cyclic Systems Attached To the 4-ring Skeleton1

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Cited by 20 publications

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“…1 H -Pyrazol-5(2 H )-ones obtained by the piperidine-promoted annulation of α-propargyl-aminohydrazones followed by solvolytic cleavage at N-1 underwent palladium-catalyzed domino vinylation/carbocyclization with steroidal enol triflates such as 97 in the presence of the Pd(OAc) 2 + dppf catalytic system (eq 72). The Z geometry of the exocyclic double bond was proved by various NMR techniques …”

Section: 2 Synthesis Of Cyclic Systems Attached To the 4-ring Skeletonmentioning

confidence: 99%

Transition-Metal-Catalyzed Reactions in Steroid Synthesis

2003

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Section: 2 Synthesis Of Cyclic Systems Attached To the 4-ring Skeletonmentioning

confidence: 99%

Transition-Metal-Catalyzed Reactions in Steroid Synthesis

2003

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“…Our recent research efforts directed toward the synthesis of functionalized heterocycles through transition-metal-catalyzed and uncatalyzed 6 domino processes led us to attain pyrroles, pyrrolo[3,2-c]pyrazolones, pyridines, quinolines, β-carbolines, naphthyridines, isoxazolo[4,5-c]quinolines, and pyrazino[1,2-a]indoles.…”

Section: Introductionmentioning

confidence: 99%

Palladium-Assisted Multicomponent Synthesis of 2-Aryl-4-aminoquinolines and 2-Aryl-4-amino[1,8]naphthyridines

et al. 2005

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A palladium-mediated multicomponent domino reaction leading to 2-aryl-4-amino-quinolines and 2-aryl-4-amino[1,8]naphthyridines is reported. The scope of the reaction was examined using carbon monoxide, two 2-ethynyl-arylamines, four aryl iodides, and 10 primary amines as substrates. The selection of the appropriate catalytic system was achieved testing several palladium/phosphine systems and overrides previously reported drawbacks associated with the use of primary amines in related reactions. Moreover several features concerning the role of both palladium [(0) and (II)] and phosphines are reported.

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Catalytic Asymmetric Synthesis of [2,3]‐Fused Indoline Heterocycles through Inverse‐Electron‐Demand Aza‐Diels–Alder Reaction of Indoles with Azoalkenes

Tong

Chen

et al. 2014

Angewandte Chemie

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Sequential Base-Promoted Annulation/Palladium-Catalyzed Domino 1,5-Enyne Arylation and Vinylation of α-Propargylaminohydrazones

Abstract: Stereoselective dominos: Cascade reactions of easily accessible α‐propargylaminohydrazones 1 represent a simple and efficient method for the preparation of pyrazolones 3.

Cited by 20 publications

References 23 publications

Transition-Metal-Catalyzed Reactions in Steroid Synthesis

Transition-Metal-Catalyzed Reactions in Steroid Synthesis

Palladium-Assisted Multicomponent Synthesis of 2-Aryl-4-aminoquinolines and 2-Aryl-4-amino[1,8]naphthyridines

Catalytic Asymmetric Synthesis of [2,3]‐Fused Indoline Heterocycles through Inverse‐Electron‐Demand Aza‐Diels–Alder Reaction of Indoles with Azoalkenes

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