T3P-Promoted Synthesis of a Series of Novel 3-Aryl-2-phenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-ones

Lee J. Silverberg; Tapas Mal; Anthony Lagalante; Mark Olsen; Michael Fleming; Tracy Garcia; Aloura Gavalis; Kyanna Gonzalez; Casey Gregory; Laine Hackenberg; Madeline Lawler; Eddie Li; Evelyn Louca; Shaheem Mack; Kristen Perhonitch; Kelsey Shaffer; Carter Thompson; Sarah Tran; Evan Vidal; Ryan Vidal

doi:10.1002/jhet.4938

T3P-Promoted Synthesis of a Series of Novel 3-Aryl-2-phenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-ones

Lee J. Silverberg, Tapas Mal, Anthony Lagalante, Mark Olsen, Michael Fleming, Tracy Garcia, Aloura Gavalis, Kyanna Gonzalez, Casey Gregory, Laine Hackenberg, Madeline Lawler, Eddie Li, Evelyn Louca, Shaheem Mack, Kristen Perhonitch, Kelsey Shaffer, Carter Thompson, Sarah Tran, Evan Vidal, Ryan Vidal

Research output: Contribution to journal › Article › peer-review

Abstract

A series of 12 novel 3-aryl-2-phenyl-2,3,5,6-tetrahydro-4H-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.

Original language	English (US)
Pages (from-to)	338-344
Number of pages	7
Journal	Journal of Heterocyclic Chemistry
Volume	62
Issue number	4
DOIs	https://doi.org/10.1002/jhet.4938
State	Published - Apr 2025

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1002/jhet.4938

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Silverberg, L. J., Mal, T., Lagalante, A., Olsen, M., Fleming, M., Garcia, T., Gavalis, A., Gonzalez, K., Gregory, C., Hackenberg, L., Lawler, M., Li, E., Louca, E., Mack, S., Perhonitch, K., Shaffer, K., Thompson, C., Tran, S., Vidal, E., & Vidal, R. (2025). T3P-Promoted Synthesis of a Series of Novel 3-Aryl-2-phenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-ones. Journal of Heterocyclic Chemistry, 62(4), 338-344. https://doi.org/10.1002/jhet.4938

@article{afaa1e26fe0541f18d92334421b459c0,

title = "T3P-Promoted Synthesis of a Series of Novel 3-Aryl-2-phenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-ones",

abstract = "A series of 12 novel 3-aryl-2-phenyl-2,3,5,6-tetrahydro-4H-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.",

author = "Silverberg, \{Lee J.\} and Tapas Mal and Anthony Lagalante and Mark Olsen and Michael Fleming and Tracy Garcia and Aloura Gavalis and Kyanna Gonzalez and Casey Gregory and Laine Hackenberg and Madeline Lawler and Eddie Li and Evelyn Louca and Shaheem Mack and Kristen Perhonitch and Kelsey Shaffer and Carter Thompson and Sarah Tran and Evan Vidal and Ryan Vidal",

note = "Publisher Copyright: {\textcopyright} 2025 The Author(s). Journal of Heterocyclic Chemistry published by Wiley Periodicals LLC.",

year = "2025",

month = apr,

doi = "10.1002/jhet.4938",

language = "English (US)",

volume = "62",

pages = "338--344",

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Silverberg, LJ , Mal, T, Lagalante, A, Olsen, M, Fleming, M, Garcia, T, Gavalis, A, Gonzalez, K, Gregory, C, Hackenberg, L, Lawler, M, Li, E, Louca, E, Mack, S, Perhonitch, K, Shaffer, K, Thompson, C, Tran, S, Vidal, E & Vidal, R 2025, 'T3P-Promoted Synthesis of a Series of Novel 3-Aryl-2-phenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-ones', Journal of Heterocyclic Chemistry, vol. 62, no. 4, pp. 338-344. https://doi.org/10.1002/jhet.4938

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T1 - T3P-Promoted Synthesis of a Series of Novel 3-Aryl-2-phenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-ones

AU - Silverberg, Lee J.

AU - Mal, Tapas

AU - Lagalante, Anthony

AU - Olsen, Mark

AU - Fleming, Michael

AU - Garcia, Tracy

AU - Gavalis, Aloura

AU - Gonzalez, Kyanna

AU - Gregory, Casey

AU - Hackenberg, Laine

AU - Lawler, Madeline

AU - Li, Eddie

AU - Louca, Evelyn

AU - Mack, Shaheem

AU - Perhonitch, Kristen

AU - Shaffer, Kelsey

AU - Thompson, Carter

AU - Tran, Sarah

AU - Vidal, Evan

AU - Vidal, Ryan

PY - 2025/4

Y1 - 2025/4

N2 - A series of 12 novel 3-aryl-2-phenyl-2,3,5,6-tetrahydro-4H-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.

AB - A series of 12 novel 3-aryl-2-phenyl-2,3,5,6-tetrahydro-4H-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.

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T3P-Promoted Synthesis of a Series of Novel 3-Aryl-2-phenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-ones

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