Three Sequential C-N Bond Formations: tert-Butyl Nitrite as a N1 Synthon in a Three Component Reaction Leading to Imidazo[1,2-a]quinolines and Imidazo[2,1-a]isoquinolines.

doi:10.1021/acs.joc.7b02815

Paper

Three Sequential C-N Bond Formations: tert-Butyl Nitrite as a N1 Synthon in a Three Component Reaction Leading to Imidazo[1,2-a]quinolines and Imidazo[2,1-a]isoquinolines.

Published Jan 8, 2018 · Prasenjit Sau, A. Rakshit, A. Modi

The Journal of organic chemistry

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22

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Abstract

tert-Butyl nitrite serves the dual role of an oxidant as well as a N1 synthon in a multicomponent reaction involving quinolines, isoquinolines, and styrenes. Herein, two sp2 C-H functionalizations of styrenes and one sp2 C-H functionalization of quinolines and isoquinolines lead to the formation of fused quinolines and isoquinolines via three sequential C-N bond formations.

Study Snapshot

Tert-Butyl nitrite serves as a N1 synthon in a multicomponent reaction leading to fused quinolines and isoquinolines through three sequential C-N bond formations.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Three Sequential C-N Bond Formations: tert-Butyl Nitrite as a N1 Synthon in a Three Component Reaction Leading to Imidazo[1,2-a]quinolines and Imidazo[2,1-a]isoquinolines.

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References

Citations

Synthetic Approaches Toward Imidazo‐Fused Heterocycles: A Comprehensive Review

This review reviews various synthetic methods for imidazo-fused heterocycles, highlighting their diverse applications and versatile chemical reactivity, and highlights future research directions.

Annulation of 1-methylisoquinoline with pyrrolylacetylenic ketones: catalyst-free stereoselective synthesis of (E)-acylethenylpyrrolo[1’,2’:3,4]imidazo[2,1-a]isoquinolines

1-Methylisoquinoline undergoes stereoselective annulation with pyrrolylacetylenic ketones to produce (E)-acylethenylpyrrolo[1',2':3,4]imidazo[2,1-a]isoquinolines in up

One-Pot Synthesis of Isoxazole-Fused Tricyclic Quinazoline Alkaloid Derivatives via Intramolecular Cycloaddition of Propargyl-Substituted Methyl Azaarenes under Metal-Free Conditions

This study developed a one-pot method for synthesis of isoxazole-fused tricyclic quinazoline alkaloids and their derivatives using propargyl-substituted methyl azaarenes under metal-free conditions.

Synthetic utility of styrenes in the construction of diverse heterocycles via annulation/cycloaddition

Styrene's unique reactivity allows for efficient synthesis of diverse heterocycles, which are crucial in various natural products, pharmaceuticals, and agrochemicals.

Iodine-Mediated Multicomponent Cascade Cyclization and Sulfenylation/Selenation: Synthesis of Imidazo[2,1-a]isoquinoline Derivatives.

This novel multicomponent cascade cyclization and sulfenylation/selenation method enables the synthesis of imidazo[2,1-a]isoquinoline derivatives in one-pot, avoiding complex substrate preparation and ensuring good substrate compatibility.