Thiazoles and their Benzo Derivatives

Metzger, Jacques

doi:10.1016/b978-008096519-2.00087-4

Cited by 129 publications

(57 citation statements)

References 165 publications

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“…Other uses of heterocyclic compounds containing nitrogen and sulfur include manufacturing biocides, dyes [22][23][24], and plant-growth regulators [25]. Thus, the synthesis of thiazole and thiadiazole derivatives is currently of great importance to the scientific community.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Novel 1,3-Thiazole and 2-Amino-1,3,4-Thiadiazole Derivatives

Şahin

Tahtacı

2014

Maced. J. Chem. Chem. Eng.

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Thiosemicarbazone derivatives 3a-e were synthesized by the reaction of various aldehydes 1a-e with 4-methyl thiosemicarbazide 2 in 78% to 90% yield. Then, the thiazole moieties of the target materials 5a-e were obtained in high yields (71-93%) using the Hantzsch reaction utilizing thiosemicarbazone derivatives 3a-e with ethyl-2-chloroacetoacetic ester. The substituted nitrile derivatives 7a-e were obtained in moderate to high yield (58-84%) from the reaction of compounds 5a-e with chloroacetonitrile by the nucleophilic aliphatic substitution reaction in the presence of anhydrous potassium carbonate. Finally, substituted 2-amino-1,3,4-thiadiazole compounds 9a-e were obtained in moderate to good yields (51-62%) from the reaction of thiosemicarbazide with substituted nitrile derivatives 7a-e. As a result, compounds that all share a high disposition for biological activities were obtained. The structures of the newly synthesized compounds were confirmed by IR, 1 H NMR, 13 C NMR, elemental analysis, and mass spectrometric techniques.Keywords: thiosemicarbazone; 1,3-thiazole; 2-amino-1,3,4-thiadiazole; Hantzsch reaction СИНТЕЗА И КАРАКТЕРИЗАЦИЈА НА НОВИ ДЕРИВАТИ НА 1,3-ТИАЗОЛ И 2-АМИНО-1,3,4-ТИАДИАЗОЛТиосемикарбазонските деривати 3a-e беа синтетизирани при реакција на разни алдехиди 1a-e со 4-метилтиосемикарбазид 2 со принос од 78 до 90%. Тиазолските прстени на целните соединенија 5a-e беа добиени со висок принос од 71-93% со реакцијата на Hantzsch со примена на тиосемикарбазонските деривати 3a-e и етил-2-хлороацетооцетен естер. Супституираните нитрилни деривати 7a-e беа добиени со умерен до висок принос при реакција на соединенијата 5a-e со хлороацетонитрил при нуклеофилна алифатична супституција во присуство на безводен калиумкарбонат. Конечно, супституираните 2-амино-1,3,4-тиодиазолните соединенија 9a-e беа добиени со умерен до добар принос (51-62%) при реакција на тиосемикарбазид со супституирани нитрилни деривати 7a-e. Сите овие добиени соединенија покажуваат висока биолошка активност. Структурите на новосинтетизираните соединенија беа потврдени по пат на IR, 1 H NMR, 13 C NMR, елементарна анализа и масеноспектрометриски техники.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Novel 1,3-Thiazole and 2-Amino-1,3,4-Thiadiazole Derivatives

Şahin

Tahtacı

2014

Maced. J. Chem. Chem. Eng.

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“…However, it is known that the exocyclic nitrogen atom of 2-aminothiazoles is the preferred site of reaction with sp 2 C electrophiles (e.g. acid chlorides, formimidates) 34,35 while the N-3 atom of 2-amino[1, 3,4]thiadiazoles has greater nucleophilicity than the exocyclic nitrogen atom, 36 so the findings described above provide consistent evidence that the chloro-substituted amidine carbon atom of 1 is the more electrophilic site.…”

Section: Scheme 14mentioning

confidence: 81%

New heteroatom-rich ring systems from N,N-dialkyl-N’-chlorosulfonyl chloroformamidines

Francis¹

2016

Arkivoc

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N,N-Dialkyl-N'-chlorosulfonyl chloroformamidines constitute a class of readily available and very versatile bis-electrophiles. This Account describes the application of these unusual + C=N-S + building blocks for construction of a cornucopia of previously unknown or uncommon heterocyclic ring systems. Regioselectivity encountered during heterocycle formation and some properties and chemistry of the newly-formed ring systems are also discussed.

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“…The richness of the pharmacopeia in compounds containing heterocyclic systems is the basis of a continuing search for versatile processes towards these key structural elements. The 1,3-thiazole ring has been identified as a central structural element of a number of biologically active natural products [5 -7] and of pharmacologically active substances [8,9]. Among various thiazolecontaining anticancer drug candidates [10], some are reported to be potential inhibitors of cyclin-dependent the reaction of N-amidinothiourea (1) with some selected electron-accepting functional groups.…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis of Thiazole, Thiazine and Isoindole Derivatives via EDA Approach and Conventional Methods

El‐Shaieb

Ameen

Abdel-Latif

et al. 2013

Zeitschrift Für Naturforschung B

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The reactivity of N-amidinothiourea (1) as an electron donor towards several electron-accepting functional groups via electron-donor-acceptor (EDA) interaction has been studied. Thus on treatment of 1 with either 1,1,2,2-tetracyanoethylene (TCNE, 2), 2,3-dicyano-1,4-naphthoquinone (DCNQ, 4), 2,3,5,6-tetrabromo-1,4-benzoquinone (BHL-p, 6), 2,3-dichloro-1,4-naphthoquinone (DCHNQ, 8), 2,3,5,6-tetrachloro-1,4-benzoquinone (CHL-p, 13), 2,3-dicyano-5,6-dichloro-1,4- benzoquinone (DDQ, 15), 2-dicyanomethyleneindan-1,3-dione (CNIND, 17), 2-(2-oxoindolin-3- ylidene)malononitrile (19), and/or dimethyl acetylenedicarboxylate (DMAD, 21), the reaction proceeds to give thiazole and thiazine derivatives, respectively. However, isoindole derivatives 24 and 26 were formed on heating of 1 with either tetrabromophthalic anhydride and=or o-phthalaldehyde, respectively. The products were fully characterized according to their spectral data. The mechanisms of formation of the products have been rationalized.

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Thiazoles and their Benzo Derivatives

Cited by 129 publications

References 165 publications

Synthesis and Characterization of Novel 1,3-Thiazole and 2-Amino-1,3,4-Thiadiazole Derivatives

Synthesis and Characterization of Novel 1,3-Thiazole and 2-Amino-1,3,4-Thiadiazole Derivatives

New heteroatom-rich ring systems from N,N-dialkyl-N’-chlorosulfonyl chloroformamidines

Facile Synthesis of Thiazole, Thiazine and Isoindole Derivatives via EDA Approach and Conventional Methods

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