Synthesis of dihydrothiazoles and thiazoles based on monothiooxamides

Yarovenko, V. N.; Polushina, A. V.; Заварзин, И. В.; Krayushkin, М. М.; Kotovskaya, S. K.; Charushin, Valery N.

doi:10.1080/17415990902774194

Cited by 8 publications

(5 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A 5-exo-dig cyclization occurs to yield a dihydrothiazole 834 . Then, a second bromine molecule reacts with the alkene to form the dibromomethyl thiazole 832 …”

Section: Reactivity Of Propargylaminesmentioning

confidence: 99%

“…Then, a second bromine molecule reacts with the alkene to form the dibromomethyl thiazole 832. 443 Two interesting approaches have been developed by Maddani and Prabhu, who reported the synthesis of a 5-methylenethiazolidine-2-thione by treatment of commercial p r o p a r g y l a m i n e w i t h m o l y b d e n u m x a n t h a t e (MoO 2 (S 2 CNMe 2 ) 2 ), 444 and by Meng and Kim, who described the synthesis of a thiazolidine derivative 835 from a Npropargylthiocarbamate through a W-and Mo-catalyzed 5-exodig cyclization reaction under irradiation at 350 nm. 445 Recently, Alhalib and Moran described the cyclization of Npropargylamides to synthesize substituted dihydrothiazoles 836.…”

Section: Synthesis Of Thiazoles and Thiazolines From Propargylaminesmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and Reactivity of Propargylamines in Organic Chemistry

et al. 2017

View full text Add to dashboard Cite

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.

show abstract

“…A 5-exo-dig cyclization occurs to yield a dihydrothiazole 834 . Then, a second bromine molecule reacts with the alkene to form the dibromomethyl thiazole 832 …”

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

View full text Add to dashboard Cite

show abstract

“…Mechanistically, the reaction involves: i) bromination of triple bond of thioamide 43 which resulted in a bridged bromonium ion intermediate A ; ii) regioselective 5- exo-dig cyclization of intermediate A to give dihydrothiazole B ; and iii) addition of a second bromine to the alkene moiety in intermediate B to provide the corresponding thiazole 44 (Scheme 11) [94]. …”

Section: Reviewmentioning

confidence: 99%

“…In 2009, Yarovenko and co-workers developed the synthesis of 5-(dibromomethyl)thiazole derivatives 44 by treatment of N -propargyl thioamides 43 with bromine in an ionic liquid (1-butyl-3-methylimidazolium hexafluorophosphate). Mechanistically, the reaction involves: i) bromination of triple bond of thioamide 43 which resulted in a bridged bromonium ion intermediate A ; ii) regioselective 5- exo-dig cyclization of intermediate A to give dihydrothiazole B ; and iii) addition of a second bromine to the alkene moiety in intermediate B to provide the corresponding thiazole 44 ( Scheme 11 ) [ 94 ].…”

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.

View full text Add to dashboard Cite

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.

show abstract

“… 4 Asymmetric propargylamines are important precursors for the synthesis of many drug molecules. 5 Annulation, cyclization and cascade transformation of various derivatives of propargylamine lead to the formation of miscellaneous heterocyclic compounds, 6 such as pyrroles, 7 pyrrolines, 8 pyrrolidine, 9 pyrazines, 10 pyrazoles, 11 thiazoles, 12 thiazolidines, 13 isoxazoles, 14 oxazolidines, 15 pyridines, 16 dihydropyridines, 17 etc.…”

Section: General Introductionmentioning

confidence: 99%