Orthogonal synthesis of densely functionalized pyrroles and thiophenes from the reactions of imidazo[1,5-a]pyridine carbene-derived zwitterions with electron-deficient alkynes.

doi:10.1021/jo100225r

Paper

Orthogonal synthesis of densely functionalized pyrroles and thiophenes from the reactions of imidazo[1,5-a]pyridine carbene-derived zwitterions with electron-deficient alkynes.

Published Mar 8, 2010 · Ying Cheng, Jiang Peng, Jiaqi Li

The Journal of organic chemistry

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Abstract

1-Thiocarbamoyl imidazo[1,5-a]pyridinium inner salts, which were obtained readily from the addition of C,N-substituted heterocyclic carbenes imidazo[1,5-a]pyridine-1-ylidenes to isothiocyanates, are powerful ambident nucleophilic zwitterions. They acted as nitrogen nucleophiles toward ethyl propiolate to produce polyfunctionalized pyrrole derivatives in high yields. When treated with dimethyl acetylenedicarboxylate, they behaved exclusively as sulfur nucleophiles to afford fully substituted thiophenes in excellent yields. This work provides highly efficient orthogonal synthesis of polyfunctionalized pyrroles and thiophenes that were not easily obtained by other chemical means.

Study Snapshot

This study presents a highly efficient orthogonal synthesis of polyfunctionalized pyrroles and thiophenes using imidazo[1,5-a]pyridine carbene-derived zwitterions with electron-deficient alkynes.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

Orthogonal synthesis of densely functionalized pyrroles and thiophenes from the reactions of imidazo[1,5-a]pyridine carbene-derived zwitterions with electron-deficient alkynes.

References

Citations

One-pot synthesis of novel 3,10-dihydro-2 H -1,3-oxazepino[7,6- b ]indoles via 1,4-dipolar cycloaddition reaction

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Exploring the nucleophilicity of N,N′-diamidocarbenes: Heteroallenes and related compounds as coupling reagents†

N,N′-diamidocarbene can react with various heteroallenes to produce various products, including acyclic triazenes and zwitterionic dihydropyrimidinium imidothiolates.

Unexpected reactivity of diaryl α-diketones with thiazolium carbenes: discovery of a novel multicomponent reaction for the facile synthesis of 1,4-thiazin-3-ones.

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Heating 2-cyanopyridine and hydrazine hydrate at 100°C with pyridine-2-carboxaldehyde produces a red semi-solid, leading to the synthesis of various 1,3-disubstituted imidazo[1,5-a]pyridines.

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-lactam carbenes can efficiently produce indeno[2,1-b]pyrrol-2-ones in a one-pot process, revealing their nucleophilicity and providing a one-pot method for efficient construction of mutisubstituted indeno[2,1-