2-Thiazolines: an update on synthetic methods and catalysis

Badillo‐Goméz, Joel I.; Gouygou, Maryse; Ortega‐Alfaro, M. Carmen; López‐Cortés, José G.

doi:10.1039/d1ob01180d

Cited by 11 publications

(2 citation statements)

References 125 publications

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“…This is the first example for the synthesis of 2,5-diarylthiazolidine through the C2-N1 bond cleavage of the indole ring. [16][17] Next, the scope of this new ring-switch reaction of indoles was evaluated by varying the substrate (Scheme 2). The effect of the substituents on the yields of the 3 was examined.…”

Section: Resultsmentioning

confidence: 99%

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Concise Synthesis of Thiazolo[4,5‐b]indoles via Ring Switch/Cyclization Sequences

Yamada,

Tsubogo,

Kanazawa

et al. 2023

Eur J Org Chem

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The unexpected reactions of indoline hemiaminals affords 2,5‐diaryl‐4‐hydroxythiazolines through a thioamidation/ring switch sequence. The key to success of this transformation is to use a thioamide as a thiazoline precursor under transient tautomeric control. This transformation features mild reaction conditions and good yields with broad functional group tolerance (17 examples, up to 99 % yield). Further transformations of the thiazolines provide a direct entry to dihydrothiazolo[4,5‐b]indoles and thiazolo[4,5‐b]indoles.

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Section: Resultsmentioning

confidence: 99%

“…[18] These sequences delineates the first example of construction of thiazoline from the indoles through the ring-switch reaction. [11][12][13][14][16][17]…”

Section: Resultsmentioning

confidence: 99%

Concise Synthesis of Thiazolo[4,5‐b]indoles via Ring Switch/Cyclization Sequences

Yamada,

Tsubogo,

Kanazawa

et al. 2023

Eur J Org Chem

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Reagent‐Controlled Chemodivergent Approach to Thiazolines and Thiazines from α‐N‐Hydroxyimino Dithioesters

et al. 2022

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A chemoselective route to thiazolines and thiazines has been devised by heterocyclization of viable α-N-hydroxyimino-β-oxodithioesters with 2-chloroethylamine hydrochloride/3-chloropropylamine hydrochloride, which does not require metals or additives and proceeds at 0-60 °C. The overall transformation involves base mediated intramolecular cyclization of α-N-hydroxyimino-β-oxodithioesters to 4-membered oxazete-4-thione intermediates followed by coupling with chloroalkyl amines via tandem ring cleavage and CÀ N/CÀ S bonds formation enabling the construction of thiazolines/thiazines in one-pot. This strategy allows broadening the arsenal of synthetic methods to obtain N,S-heterocycles utilizing substrates prepared according to reported procedures.

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Synthesis of 2‐Substituted‐4,5‐Dihydrothiazol‐4‐Ols by [3+2] Annulation of 1,4‐Dithiane‐2,5‐Diol with Thioamides

Zhang,

Chen,

Liu

et al. 2024

Asian J Org Chem

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We developed a novel method for the synthesis of 2‐substituted‐4,5‐dihydrothiazol‐4‐ols compounds through cyclization of thioamides and 1,4‐dithiane‐2,5‐diol in the presence of Et3N. Stable hydroxy‐substituted thiazole compounds were isolated of substituted thioamides. The reaction conditions are simple, the substrate range is wide, and the target compounds were obtained in up to 82% yield.

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2-Thiazolines: an update on synthetic methods and catalysis

Abstract: 2-Thiazoline is an important building block in organic synthesis and still having great importance in many areas of chemistry. At the end of the last century, the use of 2-thiazolines...

Cited by 11 publications

References 125 publications

Concise Synthesis of Thiazolo[4,5‐b]indoles via Ring Switch/Cyclization Sequences

Concise Synthesis of Thiazolo[4,5‐b]indoles via Ring Switch/Cyclization Sequences

Reagent‐Controlled Chemodivergent Approach to Thiazolines and Thiazines from α‐N‐Hydroxyimino Dithioesters

Synthesis of 2‐Substituted‐4,5‐Dihydrothiazol‐4‐Ols by [3+2] Annulation of 1,4‐Dithiane‐2,5‐Diol with Thioamides

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