Indium‐Mediated Domino Allylation‐Lactonisation Approach: Diastereoselective Synthesis of β‐Carboline C‐3 Tethered α‐Methylene γ‐Butyrolactones

Abstract

A facile and convenient tandem approach has been devised towards the diastereoselective synthesis of β‐carboline C‐3 tethered α‐methylene γ‐butyrolactones via indium‐promoted Barbier Type allylation reaction followed by in situ intramolecular lactonisation protocol. Interestingly, no additive was required for this transformation and the products were obtained with syn stereochemistry.

Indium-mediated Domino Lactonisation Approach towards Diastereoselective Synthesis of Pyrazole C-3 Linked Butyrolactones

“…The reaction was observed to be diastereoselective in nature as the single diastereomer was obtained and the stereochemistry of the pyrazole C3 tethered butyrolactone 3B across C4 and C5 proton of lactone was assigned as a syn isomer on the basis of a NOESY (2D NMR) experiment. The literature survey disclosed that THF, H2O and semiaqueous reaction medium were the best solvents for this transformation [42][43][44].…”

“…moieties Motivated by the pharmacological potential of the pyrazole and butyrolactone, it was envisaged to associate these interesting moieties in a single molecular framework via a one-pot operation. In recent past, our group successfully reported the synthesis of βcarboline and quinoline tethered butyrolactone frameworks (Figure 4) [42][43][44]. Following our previous project, we planned to explore valuable butyrolactone moiety along with the substituted pyrazole framework.…”

Harmicens, Novel Harmine and Ferrocene Hybrids: Design, Synthesis and Biological Activity

“…ISA × HCl, alcohol 5 , and aldehydes 1 and 8 were prepared according to the procedures found in the literature [ 42 , 52 , 53 ]. Amines 4 , 7 , 11 , 14 , and 17 , azides 3 and 6 , and alkynes 10 , 13 , and 16 were prepared according to our published procedures [ 31 , 32 , 33 ].…”

Et3N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties

“…In our research endeavors, we have been involved in the exploration of the synthetic potential of 1-formyl-9H-β-carboline (an alkaloid, kumujian C) [47] for preparing chemical libraries of β-carboline-substituted [48][49][50][51][52][53][54] and N-fused heterocycles [55,56] which were attributed to the presence of an electrophilic as well as a nucleophilic functionality in this natural product [1]. Encouraged by the applications of β-carboline and benzothiophene motifs in medicinal and materials chemistry, it was envisaged to construct a β-carboline-based novel molecular hybrid containing the benzothiophene moiety (Figure 1) [57,58].…”