Multicomponent Synthesis of 3-Thiazolines Using a Modified Asinger-Type Reaction

Vincent R. A. M. Reinartz; Jordy M. Saya; Darya Hadavi; Jules A. W. Harings; Romano V. A. Orru

doi:10.1021/acs.joc.5c00563

Multicomponent Synthesis of 3-Thiazolines Using a Modified Asinger-Type Reaction

Vincent R. A. M. Reinartz
, Jordy M. Saya
, Darya Hadavi
, Jules A. W. Harings
, Romano V. A. Orru^*

^*Corresponding author for this work

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

Abstract

The classical Asinger reaction is a four-component process combining sulfur, ammonia, and oxo compounds to access 3-thiazolines, but its efficiency can be hampered by in situ ammonia-derived imine formation. We report a one-pot, two-step modification using preformed trimethylsilyl-imines to efficiently yield the desired 3-thiazolines. This method tolerates a wide range of aromatic aldehydes and α-halocarbonyl compounds under microwave irradiation. Benzothiazole-3-thiazoline products undergo bond isomerization to 2-thiazolines in HFIP under elevated microwave conditions, facilitating the synthesis of (±)-firefly luciferin and related derivatives.

Original language	English
Pages (from-to)	7971-7975
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	90
Issue number	23
DOIs	https://doi.org/10.1021/acs.joc.5c00563
Publication status	Published - 13 Jun 2025

Keywords

AMMONIAK AUF KETONE
AMINES

Access to Document

10.1021/acs.joc.5c00563Licence: CC BY

Cite this

@article{ee640ab0b24c446e88c5406a2238df7a,

title = "Multicomponent Synthesis of 3-Thiazolines Using a Modified Asinger-Type Reaction",

abstract = "The classical Asinger reaction is a four-component process combining sulfur, ammonia, and oxo compounds to access 3-thiazolines, but its efficiency can be hampered by in situ ammonia-derived imine formation. We report a one-pot, two-step modification using preformed trimethylsilyl-imines to efficiently yield the desired 3-thiazolines. This method tolerates a wide range of aromatic aldehydes and α-halocarbonyl compounds under microwave irradiation. Benzothiazole-3-thiazoline products undergo bond isomerization to 2-thiazolines in HFIP under elevated microwave conditions, facilitating the synthesis of (±)-firefly luciferin and related derivatives.",

keywords = "AMMONIAK AUF KETONE, AMINES",

author = "Reinartz, \{Vincent R. A. M.\} and Saya, \{Jordy M.\} and Darya Hadavi and Harings, \{Jules A. W.\} and Orru, \{Romano V. A.\}",

year = "2025",

month = jun,

day = "13",

doi = "10.1021/acs.joc.5c00563",

language = "English",

volume = "90",

pages = "7971--7975",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "23",

}

TY - JOUR

T1 - Multicomponent Synthesis of 3-Thiazolines Using a Modified Asinger-Type Reaction

AU - Reinartz, Vincent R. A. M.

AU - Saya, Jordy M.

AU - Hadavi, Darya

AU - Harings, Jules A. W.

AU - Orru, Romano V. A.

PY - 2025/6/13

Y1 - 2025/6/13

N2 - The classical Asinger reaction is a four-component process combining sulfur, ammonia, and oxo compounds to access 3-thiazolines, but its efficiency can be hampered by in situ ammonia-derived imine formation. We report a one-pot, two-step modification using preformed trimethylsilyl-imines to efficiently yield the desired 3-thiazolines. This method tolerates a wide range of aromatic aldehydes and α-halocarbonyl compounds under microwave irradiation. Benzothiazole-3-thiazoline products undergo bond isomerization to 2-thiazolines in HFIP under elevated microwave conditions, facilitating the synthesis of (±)-firefly luciferin and related derivatives.

AB - The classical Asinger reaction is a four-component process combining sulfur, ammonia, and oxo compounds to access 3-thiazolines, but its efficiency can be hampered by in situ ammonia-derived imine formation. We report a one-pot, two-step modification using preformed trimethylsilyl-imines to efficiently yield the desired 3-thiazolines. This method tolerates a wide range of aromatic aldehydes and α-halocarbonyl compounds under microwave irradiation. Benzothiazole-3-thiazoline products undergo bond isomerization to 2-thiazolines in HFIP under elevated microwave conditions, facilitating the synthesis of (±)-firefly luciferin and related derivatives.

KW - AMMONIAK AUF KETONE

KW - AMINES

U2 - 10.1021/acs.joc.5c00563

DO - 10.1021/acs.joc.5c00563

M3 - Article

SN - 0022-3263

VL - 90

SP - 7971

EP - 7975

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 23

ER -

Multicomponent Synthesis of 3-Thiazolines Using a Modified Asinger-Type Reaction

Abstract

Keywords

Access to Document

Fingerprint

Cite this