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 | |
| State | Published - Dec 16 2016 |
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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 journal › Letter
}
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
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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U2 - 10.1021/acs.orglett.6b03199
DO - 10.1021/acs.orglett.6b03199
M3 - Letter
VL - 18
SP - 6312
EP - 6315
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 24
ER -