24 research outputs found
TOTAL SYNTHESIS OF BIOACTIVE MACROLIDES, SEIMATOPOLIDE B & (+)-CLADOSPOLIDE D AND DEVELOPMENT OF NOVEL [4+2]-BENZANNULATION REACTIONS
A Unified Strategy for the Synthesis of β‑Carbolines, γ‑Carbolines, and Other Fused Azaheteroaromatics under Mild, Metal-Free Conditions
An
efficient, unified approach for the synthesis of β-carbolines,
γ-carbolines, and other fused azaheteroaromatics has been realized
under metal-free conditions, from propargylic amines and (hetero)aromatic
aldehydes. This unified strategy provides β- and γ-carbolines
as well as a range of fused azaheteroaromatics with a broad substrate
scope and excellent functional group compatibility. The formal synthesis
of oxopropalines D and G has been achieved on gram scale (3a), in a one-pot reaction from commercially available materials (previous
shortest reported route to 3a was 5 steps). NMR studies
of the conversion of imine intermediate 3aa to β-carboline 3a were conducted and revealed that the reaction proceeded
through an allene intermediate
Rapid Access to 3Substituted Pyridines and Carbolines via a Domino, Copper-free, Palladium-Catalyzed Sonogashira Cross-Coupling/6-Aza Cyclization Sequence
Herein,
we report a one-pot, three-component method for the preparation
of 3-substituted pyridines and carbolines via copper-free, palladium-catalyzed
Sonogashira cross-coupling with aryl iodides, followed by 6π-aza
cyclization. This arylation cross-coupling/annulation cascade provides
easy access to substituted, fused pyridines from readily available
substrates in good yields (67–92%) with complete selectivity
ChemInform Abstract: One‐Pot Sequential Propargylation/Cycloisomerization: A Facile [4 + 2]‐Benzannulation Approach to Carbazoles.
ChemInform Abstract: Novel [4 + 2]‐Benzannulation to Access Substituted Benzenes and Polycyclic Aromatic and Benzene‐Fused Heteroaromatic Compounds.
A general method for the metal-free, regioselective, remote C–H halogenation of 8-substituted quinolines
An operationally simple, metal-free protocol for regioselective halogenation of a range of 8-substituted quinolines has been established using recyclable trihaloisocyanuric acids.</p
