Convenient one-pot formation of highly functionalized 5-bromo-2-aminothiazoles, potential endocannabinoid hydrolase MAGL inhibitors

Prévost, Julien R. C.; Kozlova, Arina; Saadi, Bouazza Es; Yıldız, Esra; Modaffari, Sara; Lambert, Didier M.; Pochet, Lionel; Dolušić, Eduard; Frédérick, Raphaël

doi:10.1016/j.tetlet.2018.10.055

Cited by 12 publications

(4 citation statements)

References 42 publications

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“…Prevost and coworkers developed a protocol for obtaining 5‐bromo‐2‐amino‐1,3‐thiazoles ( 175 ) by using 2‐bromo acetophenone ( 173 ) and substituted thiourea ( 174 ) at room temperature. They also obtained the non‐brominated thiazole ( 176 ) as a byproduct in this reaction condition.…”

Section: Synthesis Of Thiazolesmentioning

confidence: 99%

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An Overview of Recent Developments in the Synthesis of Substituted Thiazoles

et al. 2020

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Thiazole frame work represents a vital pharmacophore in several areas of chemistry. Consequently, several synthetic protocols to construct and functionalize this core, in an attempt to generate diverse thiazole containing architectures have been developed by various researchers across the globe. These wide range of methodologies developed will allow the access to fully decorated thiazole containing new chemical entities that can find various application in the field of medicinal chemistry, agrochemicals and material science. This review will provide an insight in to the various synthons used in construction and diversification of this core. Diversely functionalized thiazole analogs are considered as a vital azole framework present in many natural products. This prominent heterocycle also constitutes an important pharmacophore in medicinal chemistry, in agrochemicals and in molecules for material science applications. All these above‐mentioned features of thiazole necessitates the continuous development of efficient methods to access this heterocycle. Accordingly, various researchers across the globe have come up with efficient synthetic protocols in an attempt functionalize different positions of this important scaffold. This review aims at highlighting some of the latest synthetic approaches to di/tri‐substituted thiazole analogs which are known to possess a wide spectrum of biological activities.

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Section: Synthesis Of Thiazolesmentioning

confidence: 99%

“…Dalip Kumar et al [39] reported a green protocol for accessing substituted thiazoles (75), that utilizes α-tosyloxy ketones (73) and diverse thioamides (74). The presence of aryl groups on compound 74 resulted in better yields when compared to heteroaryl groups (Scheme 24).…”

Section: Thioamidesmentioning

confidence: 99%

An Overview of Recent Developments in the Synthesis of Substituted Thiazoles

et al. 2020

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“…So far, few 5-substituted N-4-diaryl 2-aminothiazoles have been structurally characterized, viz. ANTZOB (Declercq et al, 1981), QAWDAT (Schantl & Lagoja, 1998), VAZNEQ (Shao et al, 2006), TIHKOL (Dridi & El Efrit, 2007), XIVCAJ and XIVCEN (Prevost et al, 2018). As far as we are able to ascertain, there are no published crystal structures of related 5-carboxylate N-4-diaryl 2-aminothiazoles, and just two for 5-carboxylate N,N-4-triaryl-2-aminothiazoles, NIBDEJ (Souldozi et al, 2013) and USAQIQ (Heydari et al, 2016), in which the formal C O group adopts an orientation antiperiplanar to the adjacent thiazole C-S bond, in contrast to 3 and 4.…”

Section: Tablementioning

confidence: 99%

A solid solution of ethyl andd₃-methyl 2-[(4-methylpyridin-2-yl)amino]-4-(pyridin-2-yl)thiazole-5-carboxylate

Beuchel¹,

Goddard²,

Imming³

et al. 2020

Acta Cryst E

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The synthesis of ethyl 2-[(4-methylpyridin-2-yl)amino)-4-(pyridin-2-yl)thiazole- 5-carboxylate via the Hantzsch reaction and partial in situ transesterification during recrystallization from methanol-d 4 to the d 3-methyl ester, resulting in the title solid solution, ethyl 2-[(4-methylpyridin-2-yl)amino)-4-(pyridin-2-yl)thiazole-5-carboxylate–d 3-methyl 2-[(4-methylpyridin-2-yl)amino)-4-(pyridin-2-yl)thiazole-5-carboxylate (0.88/0.12), 0.88C17H16N4O2S·0.12C16D3H11N4O2S, is reported. The refined ratio of ethyl to d 3-methyl ester in the crystal is 0.880 (6):0.120 (6). The pyridine ring is significantly twisted out of the plane of the approximately planar picoline thiazole ester moiety. N—H...N hydrogen bonds between the secondary amino group and the pyridine nitrogen atom of an adjacent symmetry-related molecule link the molecules into polymeric hydrogen-bonded zigzag tapes extending by glide symmetry in the [001] direction. There is structural evidence for intramolecular N...S chalcogen bonding and intermolecular weak C—H...O hydrogen bonds between adjacent zigzag tapes.

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“…Several methods for the synthesis of thiazoles and their derivatives were developed by various catalysts, conditions, and strategies [12][13][14][15][16][17][18][19][20][21]. From these methods, we were interested in the synthesis of thiazoles by condensation of α-halo ketones with thioamides [22][23][24][25][26][27][28]. Beyzaei et al reported the one-pot synthesis of thiazol-2(3H)-imines through nucleophilic substitution of chloride in 3chloroacetylacetone with thiocyanate group followed by cyclo condensation with various hydrazine or hydrazide derivatives.…”

Section: Introductionmentioning

confidence: 99%

Facile one-pot synthesis of thiazol-2(3H)-imine derivatives from α-active methylene ketones.

El-Sawah

Loksha

Elrazaz

et al. 2020

Archives of Pharmaceutical Sciences Ain Shams University

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Convenient one-pot formation of highly functionalized 5-bromo-2-aminothiazoles, potential endocannabinoid hydrolase MAGL inhibitors

Cited by 12 publications

References 42 publications

An Overview of Recent Developments in the Synthesis of Substituted Thiazoles

An Overview of Recent Developments in the Synthesis of Substituted Thiazoles

A solid solution of ethyl andd₃-methyl 2-[(4-methylpyridin-2-yl)amino]-4-(pyridin-2-yl)thiazole-5-carboxylate

Facile one-pot synthesis of thiazol-2(3H)-imine derivatives from α-active methylene ketones.

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Convenient one-pot formation of highly functionalized 5-bromo-2-aminothiazoles, potential endocannabinoid hydrolase MAGL inhibitors

Cited by 12 publications

References 42 publications

An Overview of Recent Developments in the Synthesis of Substituted Thiazoles

An Overview of Recent Developments in the Synthesis of Substituted Thiazoles

A solid solution of ethyl andd3-methyl 2-[(4-methylpyridin-2-yl)amino]-4-(pyridin-2-yl)thiazole-5-carboxylate

Facile one-pot synthesis of thiazol-2(3H)-imine derivatives from α-active methylene ketones.

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A solid solution of ethyl andd₃-methyl 2-[(4-methylpyridin-2-yl)amino]-4-(pyridin-2-yl)thiazole-5-carboxylate