TBAI/TBHP-catalyzed [3 + 2]cycloaddition/oxidation/aromatization cascade and online ESI-MS mechanistic studies: synthesis of pyrrolo[2,1-a]isoquinolines and indolizino[8,7-b]indoles

Abstract

In the reaction of 3,4‐dihydroquinoline (IX) an aromatization is observed which does not take place using isoquinolines.

Post‐Pictet‐Spengler Cyclization (PPSC): A Strategy to Synthesize Polycyclic β‐Carboline‐Derived Natural Products and Biologically Active N‐Heterocycles

“…Nekkanti et al. developed a protocol for the synthesis of penta/hexacyclic heterocycles having common dihydroindolizino[8,7‐ b ]indole motif using [3+2] cycloaddition as a key step (Scheme ) . During the course of reaction, [3+2] cycloaddition, oxidation and aromatization occurred in cascade manner and the reaction intermediates within this cascade were characterized by realtime monitoring of reaction using ESI‐MS.…”

Reliability of Click Chemistry on Drug Discovery: A Personal Account

“…The pyrrolo[2,1‐ a ]isoquinoline 90 and indolizino[8,7‐ b ]indole 92 represents the core structure of various alkaloids which exhibits a wide spectrum of biological activities. Considering their biological and pharmaceutical relevance, in 2016, we have reported the synthesis of these skeletons through [3+2] cycloaddition using TBAI/TBHP catalysis . In recent times, TBAI/TBHP catalytic system has gained distinctive consideration owing to its simple operation, high efficiency, non‐toxicity, cost‐effectiveness and eco‐friendliness .…”

A new approach to alkaloid-like systems: synthesis and crystal structure of 1-(2-acetyl-11-methoxy-5,6-dihydro[1,3]dioxolo[4,5-g]pyrrolo[2,1-a]isoquinolin-1-yl)propan-2-one

“…The dihydropyrrolo[2,1-a]isoquinoline skeleton can be constructed in two different ways. The first way is annelation of a pyrrole ring to an isoquiniline fragment (Ma et al, 2014;Fujiya et al, 2016;Nekkanti et al, 2016). The second one, in contrast, is annelation of an isoquiniline fragment to pyrrole derivatives (Sun et al, 2012;Wiest et al, 2016).…”