Abstract
Thioamides bearing electron-withdrawing groups on the thiocarbonyl carbon atom react with benzynes [generated by the hexadehydro-Diels-Alder cycloisomerization] in an unprecedented fashion. Namely, the dihydrobenzothiazole products are consistent with a pathway involving initial formation of a stabilized ammonium ylide by a rare type of [3 + 2]-cycloaddition reaction. The fate of this species depends upon the nature of the R group(s) attached to the ylide nitrogen atom. The demonstration of new modes of reactivity represents the major advance arising from this study.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 5550-5553 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 20 |
| Issue number | 18 |
| DOIs | |
| State | Published - Sep 21 2018 |
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 (R01 GM65597, then R35 GM127097). A.C.S.P. and V.P. appreciate the support of a Gleysteen−Heisig fellowship for undergraduate students. Some of the NMR data were obtained with an instrument acquired with funds from the NIH Shared Instrumentation Grant program (S10OD011952).
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 (R01 GM65597, then R35 GM127097). A.C.S.P. and V.P. appreciate the support of a Gleysteen-Heisig fellowship for undergraduate students. Some of the NMR data were obtained with an instrument acquired with funds from the NIH Shared Instrumentation Grant program (S10OD011952).
Publisher Copyright:
Copyright © 2018 American Chemical Society.