Reactions of Hexadehydro-Diels-Alder (HDDA)-Derived Benzynes with Thioamides

Synthesis of Dihydrobenzothiazino-Heterocyclics

Vignesh Palani, Junhua Chen, Thomas R Hoye

Research output: Contribution to journalLetter

13 Citations (Scopus)

Abstract

Reaction of thioamides (e.g., II) with benzynes generated by the hexadehydro-Diels-Alder (HDDA) cycloisomerization (e.g., I) produces dihydrobenzothiazines (e.g., III). It is postulated that the reaction proceeds via benzothietene (cf. IV) and o-thiolatoaryliminium (cf. V) intermediates and that the latter undergoes intramolecular 1,3-hydrogen atom migration to produce the penultimate isomeric iminium zwitterions VI.

Original languageEnglish (US)
Pages (from-to)6312-6315
Number of pages4
JournalOrganic Letters
Volume18
Issue number24
DOIs
StatePublished - Dec 16 2016

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Thioamides
Cycloaddition Reaction
Hydrogen
Atoms
zwitterions
synthesis
hydrogen atoms

Cite this

Reactions of Hexadehydro-Diels-Alder (HDDA)-Derived Benzynes with Thioamides : Synthesis of Dihydrobenzothiazino-Heterocyclics. / Palani, Vignesh; Chen, Junhua; Hoye, Thomas R.

In: Organic Letters, Vol. 18, No. 24, 16.12.2016, p. 6312-6315.

Research output: Contribution to journalLetter

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abstract = "Reaction of thioamides (e.g., II) with benzynes generated by the hexadehydro-Diels-Alder (HDDA) cycloisomerization (e.g., I) produces dihydrobenzothiazines (e.g., III). It is postulated that the reaction proceeds via benzothietene (cf. IV) and o-thiolatoaryliminium (cf. V) intermediates and that the latter undergoes intramolecular 1,3-hydrogen atom migration to produce the penultimate isomeric iminium zwitterions VI.",
author = "Vignesh Palani and Junhua Chen and Hoye, {Thomas R}",
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T1 - Reactions of Hexadehydro-Diels-Alder (HDDA)-Derived Benzynes with Thioamides

T2 - Synthesis of Dihydrobenzothiazino-Heterocyclics

AU - Palani, Vignesh

AU - Chen, Junhua

AU - Hoye, Thomas R

PY - 2016/12/16

Y1 - 2016/12/16

N2 - Reaction of thioamides (e.g., II) with benzynes generated by the hexadehydro-Diels-Alder (HDDA) cycloisomerization (e.g., I) produces dihydrobenzothiazines (e.g., III). It is postulated that the reaction proceeds via benzothietene (cf. IV) and o-thiolatoaryliminium (cf. V) intermediates and that the latter undergoes intramolecular 1,3-hydrogen atom migration to produce the penultimate isomeric iminium zwitterions VI.

AB - Reaction of thioamides (e.g., II) with benzynes generated by the hexadehydro-Diels-Alder (HDDA) cycloisomerization (e.g., I) produces dihydrobenzothiazines (e.g., III). It is postulated that the reaction proceeds via benzothietene (cf. IV) and o-thiolatoaryliminium (cf. V) intermediates and that the latter undergoes intramolecular 1,3-hydrogen atom migration to produce the penultimate isomeric iminium zwitterions VI.

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