Overview of the Chemistry of 2-Thiazolines

Gaumont, Annie‐Claude; Gulea, Mihaela; Levillain, Jocelyne

doi:10.1021/cr800189z

Cited by 171 publications

(96 citation statements)

References 243 publications

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“…Treatment of commercially available L-cystine (6) Firstly, the (R)-enantiomer of bacillamide B (12, Scheme 3) was synthesized from (R)-2-(tert-butyldiphenylsilyloxy)lactic acid (10) following the same procedure as described in the preparation of (S)-bacillamide B (2). The specific optical rotation of our 12 was measured as [α] 20 D = +2.01 (c 0.095, MeOH), having the same sign as those from literature data.…”

Section: Resultsmentioning

confidence: 99%

“…All reactions under standard conditions were monitored by thin-layer chromatography (TLC) on gel F 254 plates. 1 H NMR (400 MHz) and 13 C NMR (100 MHz) spectra were recorded using CDCl 3 or DMSO-d 6 as the solvent, and chemical shifts are reported as δ values in ppm based on internal (CH 3 ) 4 Si (0.00 ppm) or solvent peak. Multiplicity is tabulated as s for singlet, d for doublet, t for triplet, q for quadruplet, and m for multiplet, whereby the prefix app is applied in cases where the true multiplicity is unresolved, and br when the signal is broadened.…”

Section: Generalmentioning

confidence: 99%

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Synthesis and structural reconfirmation of bacillamide B

Sun

Liu

et al. 2015

Org. Biomol. Chem.

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A concise total synthesis of the natural product bacillamide B was accomplished in 30% overall yield starting from L-cystine. The key step was a one-pot four-step process of thiazoline formation via a cascade disulfide cleavage/thiocarbonylation/Staudinger reduction/aza-Wittig reaction using β-azido disulfide and carboxylic acid as substrates. The absolute configuration of the natural bacillamide B was reconfirmed to be S and the specific optical rotation was revised to (−).

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Section: Resultsmentioning

confidence: 99%

Section: Generalmentioning

confidence: 99%

Synthesis and structural reconfirmation of bacillamide B

Sun

Liu

et al. 2015

Org. Biomol. Chem.

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“…Infrared spectra were recorded on a Perkin Elme r 14 spectrometer using potassium bro mide Waffer technique. 1 H NMR spectra were measured on a Bruker WP 300 in CDCl 3 , DMSO or CF 3 COOD as solvent, using TMS as an internal standard. Mass spectra were recorded on a Finnigan MAT 212 instrument.…”

Section: Materials and Instrumentationmentioning

confidence: 99%

“…The chemistry of 2-th iazo lines, including new methodologies for their preparation, and recent applicat ions, such as their growing use in organic synthesis in the biological field and asymmetric catalysis as ligands has been recently reviewed [1]. 2-A minothiazo les are known main ly as biologically active co mpounds with a broad range of activity and as intermed iates in the synthesis of antibiotics and dyes [2].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Some New 5-Arylazothiazole Derivatives as Disperse Dyes for Dyeing Polyester Fibers

Khalifa¹,

Abdel‐Latif²,

Amer³

et al. 2013

TEXTILE

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A series of 5-arylazo-2-(arylidenehydrazino)-2-th iazo lin -4-one dyes 3 and 4 was prepared by cyclocondensation of hydrazonoyl bro mides 2 with various thiosemicarbazone derivatives 1. While the synthesis of 3-amino-N-(5-aryla zo-2-thiazo lyl)-thieno[2,3-b]pyrid ine-2-carbo xamide dyes 8 was achieved by the reaction of 2-(N-chloroacetyl)-5-ary lazo -thiazo le derivatives 5 with 4,6-dimethyl-2-mercaptonicotinonitrile fo llowed by heterocyclizat ion of the obtained sulfide derivatives 7 in a solution of ethanol containing sodium etho xide. These dyes were applied as disperse dyes for dyeing polyester fibers and their characteristics and fastness properties have been measured. The dyed fibers exh ibit very good to excellent washing, perspiration and sublimat ion fastness properties, with little variation in good to excellent rubbing and light fastness.

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“…The chemistry of thiazo le derivatives, including new methodologies for their preparation, and recent applicat ions, such as their growing use in organic synthesis in the biological field and asymmetric catalysis as ligands has been recently reviewed [1]. Th iazo lidinones are known main ly as biologically active co mpounds with a broad range of activity and as intermediates in the synthesis of antibiotics and dyes [2][3][4].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Some New Functionalized Bis-thiazolidin-5-one and Bis-thiazolidin-4-one Derivatives

Metwally¹,

Fekri²,

Nagy³

et al. 2012

CHEMISTRY

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A series of bis-thiazo lidin-5-one and bis-thiazo lid in-4-one derivatives 3and5 was prepared by the treatment of highly functional thiocarbamoyl intermediates 2 and 4 with chloroacetyl chloride and chloroacetic acid, respectively. Treat ment of the bis-thiocarbamoyl derivative 4a with diazotized sulphanilic acid affected acetyl cleavage to afford the corresponding arylhydrazono-thiocarbamoyl derivative 6.The tit le co mpounds bis-thiazolid in-5-one and bis-thiazolidin -4-one derivatives showed high reactiv ity towards azo coupling react ion with diazotized sulphanilic acid and Knoevenagel reaction with 4-isopropylbenzaldehyde.

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Overview of the Chemistry of 2-Thiazolines

Cited by 171 publications

References 243 publications

Synthesis and structural reconfirmation of bacillamide B

Synthesis and structural reconfirmation of bacillamide B

Synthesis of Some New 5-Arylazothiazole Derivatives as Disperse Dyes for Dyeing Polyester Fibers

Synthesis of Some New Functionalized Bis-thiazolidin-5-one and Bis-thiazolidin-4-one Derivatives

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