Propargylamine–isothiocyanate reaction: efficient conjugation chemistry in aqueous media

Viart, Helene Marie-France; Larsen, T. S.; Tassone, Chiara; Andresen, Thomas Lars; Clausen, Mads Hartvig

doi:10.1039/c4cc00863d

Cited by 17 publications

(11 citation statements)

References 14 publications

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“…The fluorescein-thiazolidines 813 were obtained under mild conditions (20 °C, water and tert-butanol) with excellent yields (78–81%). The reaction progress was also monitored, and it was found that a mixture of thiourea and thiazolidine (2:3 ratio) intermediates were formed after 3 h, but after 24 h, only the thiazolidine products remained, implying a successive two-step reaction mechanism …”

Section: Reactivity Of Propargylaminesmentioning

confidence: 99%

“…The reaction progress was also monitored, and it was found that a mixture of thiourea and thiazolidine (2:3 ratio) intermediates were formed after 3 h, but after 24 h, only the thiazolidine products remained, implying a successive two-step reaction mechanism. 435 Finally, Beauchemin and co-workers reported the syntheses of a series of substituted thiazolidines 816 using Nisothiocyanate precursors 814. Treatment of 814 with a base (Et 3 N) under microwave irradiation led to the formation of the isothiocyanate intermediate 815, which in turn reacts with propargylamines to afford thiazolidines 816 in good yields.…”

Section: Synthesis Of Thiazoles and Thiazolines From Propargylaminesmentioning

confidence: 99%

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Synthesis and Reactivity of Propargylamines in Organic Chemistry

et al. 2017

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Propargylamines are a versatile class of compounds which find broad application in many fields of chemistry. This review aims to describe the different strategies developed so far for the synthesis of propargylamines and their derivatives as well as to highlight their reactivity and use as building blocks in the synthesis of chemically relevant organic compounds. In the first part of the review, the different synthetic approaches to synthesize propargylamines, such as A couplings and C-H functionalization of alkynes, have been described and organized on the basis of the catalysts employed in the syntheses. Both racemic and enantioselective approaches have been reported. In the second part, an overview of the transformations of propargylamines into heterocyclic compounds such as pyrroles, pyridines, thiazoles, and oxazoles, as well as other relevant organic derivatives, is presented.

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Section: Reactivity Of Propargylaminesmentioning

confidence: 99%

Section: Synthesis Of Thiazoles and Thiazolines From Propargylaminesmentioning

confidence: 99%

Synthesis and Reactivity of Propargylamines in Organic Chemistry

et al. 2017

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“…Seeking for a greener approach towards thiazolidines of type 30 , the group of Clausen has proposed a base-catalyzed protocol using t -BuOH in water at 20 °C for a quite efficient cyclization between secondary N -propargylamines 28 and fluorescein isothiocyanate 29 ( Scheme 7 ) [ 89 ].…”

Section: Reviewmentioning

confidence: 99%

N-Propargylamines: versatile building blocks in the construction of thiazole cores

Arshadi

Vessally

Edjlali

et al. 2017

Beilstein J. Org. Chem.

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Thiazoles and their hydrogenated analogues are not only key structural units in a wide variety of natural products but they also constitute important building blocks in medicinal chemistry. Therefore, the synthesis of these compounds using new protocols is always interesting. It is well known that N-propargylamines can undergo a number of cyclization reactions to produce various nitrogen-containing heterocycles. In this review, we highlight the most important developments on the synthesis of thiazole and its derivatives starting from N-propargylamines. This review will be helpful in the development of improved methods for the synthesis of natural and biologically important compounds.

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“… 15 Coupling of oligoethylene glycol mesylates 5–9 with compound 1 with gave the corresponding BTA dimers 13–17 ( Scheme 2 ), and the final products were purified by HPLC. 16 …”

Section: Resultsmentioning

confidence: 99%