Advancing the Morita–Baylis–Hillman Chemistry of 1‐Formyl‐β‐carbolines for the Synthesis of Indolizino‐indole Derivatives

Abstract

The chemistry of the Morita-Baylis-Hillman adducts of 1-formyl-β-carbolines has been extended for obtaining indolizino-indole derivatives which mimic the harmicine and homofascaplysin frameworks. Adducts of N-substituted methyl 1-formyl-9H-β-carboline-3-carboxylate yield indolizino-indole derivatives upon bromination followed by aqueous workup. On the other hand, N-substituted 1-formyl-9H-β-carbolines give rise to similar products in a one-pot DABCO-promoted

Synthesis of chitosan‐graft‐poly[2‐cyano‐1‐(pyridin‐3‐yl)allyl acrylate] copolymer from a novel monomer, prepared using a Morita–Baylis–Hillman reaction, and characterization of its antimicrobial activity

“…The chitosan graft copolymer, Cs‐PCPA, was prepared by a route that begins with the synthesis of the monomer CPA. For this purpose, HPA was generated using the DABCO‐catalysed Morita–Baylis–Hillman reaction between acrylonitrile and nicotinaldehyde (Scheme ) . The product of this reaction, HPA, whose structure was assigned using X‐ray crystallographic analysis (Fig.…”

1-Formyl-9H-β-Carboline: A Useful Scaffold for Synthesizing Substituted- and Fused β-Carbolines

“…In addition to annulation between C-1 and N-9, we also disclosed the potential of N-alkylated 1-formyl-9H--carboline to accomplish the annulation between C-1 and N-2 to produce indolizinoindole derivatives as depicted in Scheme 31 and 32 [30]. The N-alkylated derivatives (70-71 and 89) upon MBH reaction with various acrylates and cycloalkenones in the presence of DABCO or DMAP afforded the MBH adducts (81, 90-91, and 94).…”

Chemistry of β‐Carbolines as Synthetic Intermediates

“…[36] In a separate contribution the MBH adducts 22 were subjected to bromination and cyclization to afford compounds 23 with the homofascaplysin framework. [37] Scheme 22.…”