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.

Publisher link

10.1021/acs.orglett.6b03199

http://europepmc.org/articles/pmc5629071

Find It

Find It at U of M Libraries

Cite this

@article{991da35b5c064586a11abe20e7b86cce,

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.",

year = "2016",

month = dec,

day = "16",

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

language = "English (US)",

volume = "18",

pages = "6312--6315",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "24",

}

TY - JOUR

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.

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.

UR - http://www.scopus.com/inward/record.url?scp=85006482135&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85006482135&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.6b03199

DO - 10.1021/acs.orglett.6b03199

M3 - Letter

C2 - 27978648

AN - SCOPUS:85006482135

VL - 18

SP - 6312

EP - 6315

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 24

ER -

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

Abstract

Bibliographical note

Publisher link

Find It

Other files and links

Fingerprint

Cite this