Employing Arynes in Transition-Metal-Free, N-Heterocycle- Initiated Multicomponent Reactions

Anup Bhunia; Akkattu T. Biju

doi:10.1055/s-0033-1340549

Synlett, Inhaltsverzeichnis

Synlett 2014; 25(5): 608-614
DOI: 10.1055/s-0033-1340549

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Employing Arynes in Transition-Metal-Free, N-Heterocycle- Initiated Multicomponent Reactions

Anup Bhunia

Organic Chemistry Division, CSIR-National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune 411008, India Fax: +91(20)25902629 eMail: at.biju@ncl.res.in

,

Akkattu T. Biju*

Organic Chemistry Division, CSIR-National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune 411008, India Fax: +91(20)25902629 eMail: at.biju@ncl.res.in

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Abstract

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Abstract

Transition-metal-free multicomponent reactions involving arynes, N-heterocycles, and various carbonyl compounds have been reported. With (iso)quinoline as the nucleophile and carbonyl compounds, such as aldehydes, ketones, and N-substituted isatins as electrophiles, the reaction afforded oxazino (iso)quinoline derivatives and the reaction proceeded via 1,4-dipolar intermediates. Interestingly, when the nucleophilic trigger used is pyridine, the reaction furnished indolin-2-one derivatives, and it is probable that the reaction proceeds via a pyridylidene intermediate.

Key words

arynes - multicomponent reaction - oxindoles - pyridines - quinolines

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Referenzen

References and Notes

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