Abstract
1-(1,3-Dithian-2-yl)propargylamines undergo iodo-cylization regioselectively to afford tetrasubstituted 3-amino-4-iodothiophenes in 30–87 % yields by iodide induced cleavage of dithiane ring in a bicyclic sulfonium intermediate. A mechanism for this unprecedented transformation was proposed and tentatively supported by the isolation of an intermediate structure. 1-(1,3-Dithian-2-yl)propargylamines were prepared in 30–94 % yields by Au-catalyzed one-pot, three-component reaction of 1,3-dithiane-2-carbaldehydes, amines, and alkynes so called A3-coupling reaction.
| Original language | English |
|---|---|
| Pages (from-to) | 4107-4124 |
| Number of pages | 18 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2021 |
| Issue number | 29 |
| DOIs | |
| Publication status | Published - 6 Aug 2021 |
Bibliographical note
Publisher Copyright:© 2021 Wiley-VCH GmbH
Funding
This study was funded by The Scientific and Technological Research Council of Turkey (TUBITAK) (project no. KBAG‐119Z533). We would like to thank TUBITAK for its support. Authors thank to Research Board of Istanbul Technical University and METU Central Laboratory for HRMS measurements and Giresun University Central Laboratory for X‐ray single crystal diffraction measurements. Authors also thank to Dr. Armagan Atsay for NMR measurements. This study was funded by The Scientific and Technological Research Council of Turkey (TUBITAK) (project no. KBAG-119Z533). We would like to thank TUBITAK for its support. Authors thank to Research Board of Istanbul Technical University and METU Central Laboratory for HRMS measurements and Giresun University Central Laboratory for X-ray single crystal diffraction measurements. Authors also thank to Dr. Armagan Atsay for NMR measurements.
| Funders | Funder number |
|---|---|
| METU | |
| TUBITAK | KBAG‐119Z533 |
| Türkiye Bilimsel ve Teknolojik Araştirma Kurumu | |
| Istanbul Teknik Üniversitesi |
Keywords
- 1,3-Dithiane
- A-coupling
- Iodocyclization
- Iodothiophene
- Sulfonium ion