<scp>T3P</scp>‐Promoted Synthesis of a Series of Novel 3‐Aryl‐2‐phenyl‐2,3,5,6‐tetrahydro‐<scp>4<i>H</i></scp>‐1,3‐thiazin‐4‐ones
ABSTRACT A series of 12 novel 3‐aryl‐2‐phenyl‐2,3,5,6‐tetrahydro‐4 H ‐1,3‐thiazin‐4‐ones was prepared at room temperature by T3P‐mediated cyclization of C ‐phenyl‐ N ‐aryl imines with 3‐mercaptopropionic acid. Both electron‐withdrawing and electron‐donating substituents were used. All substituents were successful, including p ‐nitro. Some reactions were run as 3‐component reactions, forming the imine in situ. The reactions were operationally simple and gave yields as high as 79%. An example was also done where a p ‐nitro group was on both the C ‐aryl and the N ‐aryl. This provides ready access to N ‐aryl compounds in this family, which have been generally difficult to prepare.
Authors
- Craig S. M. Thompson
- Steven Mack
- Casey L. Gregory (ORCID: https://orcid.org/0000-0002-9332-0841)
- Ephraim S. Vidal
- Mark A. Olsen
- Lee J. Silverberg (ORCID: https://orcid.org/0000-0002-7353-1289)
- E. P.-M. Li
- Sarah Tran (ORCID: https://orcid.org/0000-0002-9438-1910)
- Anthony F. Lagalante (ORCID: https://orcid.org/0000-0003-4684-0307)
- Tapas K. Mal (ORCID: https://orcid.org/0000-0002-0625-2095)
- Kristen C. Perhonitch
- Kyanna M. Gonzalez
- Tracy L. Garcia
- Kelsey N. Shaffer
- Evelyn M. Louca
- Aloura D. Gavalis
- Michael Fleming
- Rosário Vidal
- Laine Hackenberg
- Madeline Lawler
Institutions
- Pennsylvania State University (US)
- Federal Correctional Institution Schuylkill (US)
- Villanova University (US)
Publication Details
- Journal
- Journal of Heterocyclic Chemistry
- Published
- 2025-01-09
- DOI
- https://doi.org/10.1002/jhet.4938
- Primary Topic
- Phenothiazines and Benzothiazines Synthesis and Activities
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Science Foundation
- University of Pennsylvania
- Villanova University
- Pennsylvania State University
- Division of Chemistry