Reactions of Hexadehydro-Diels-Alder (HDDA)-Derived Benzynes with Thioamides: Synthesis of Dihydrobenzothiazino-Heterocyclics

Vignesh Palani; Junhua Chen; Thomas R. Hoye

doi:10.1021/acs.orglett.6b03199

Reactions of Hexadehydro-Diels-Alder (HDDA)-Derived Benzynes with Thioamides: Synthesis of Dihydrobenzothiazino-Heterocyclics

Vignesh Palani, Junhua Chen, Thomas R. Hoye

Chemistry (Twin Cities)

Research output: Contribution to journal › Letter › peer-review

18 Scopus citations

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 language	English (US)
Pages (from-to)	6312-6315
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	24
DOIs	https://doi.org/10.1021/acs.orglett.6b03199
State	Published - Dec 16 2016

Bibliographical note

Funding Information:
Support for this research was provided by the National Institutes of General Medical Sciences of the U.S. Department of Health and Human Services (GM65597). V.P. appreciates support from a Gleysteen?Heisig fellowship for undergraduate students. Some of theNMRdata were obtained with an instrument acquired with funds from the NIH Shared Instrumentation Grant program (S10OD011952).

Publisher Copyright:
© 2016 American Chemical Society.

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title = "Reactions of Hexadehydro-Diels-Alder (HDDA)-Derived Benzynes with Thioamides: Synthesis of Dihydrobenzothiazino-Heterocyclics",

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.}",

note = "Funding Information: Support for this research was provided by the National Institutes of General Medical Sciences of the U.S. Department of Health and Human Services (GM65597). V.P. appreciates support from a Gleysteen?Heisig fellowship for undergraduate students. Some of theNMRdata were obtained with an instrument acquired with funds from the NIH Shared Instrumentation Grant program (S10OD011952). Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

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doi = "10.1021/acs.orglett.6b03199",

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AU - Chen, Junhua

AU - Hoye, Thomas R.

N1 - Funding Information: Support for this research was provided by the National Institutes of General Medical Sciences of the U.S. Department of Health and Human Services (GM65597). V.P. appreciates support from a Gleysteen?Heisig fellowship for undergraduate students. Some of theNMRdata were obtained with an instrument acquired with funds from the NIH Shared Instrumentation Grant program (S10OD011952). Publisher Copyright: © 2016 American Chemical Society.

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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Reactions of Hexadehydro-Diels-Alder (HDDA)-Derived Benzynes with Thioamides: Synthesis of Dihydrobenzothiazino-Heterocyclics

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