Utility of thiocarbamoyl moiety in synthesis of some new sulphur containing heterocyclic compounds and evaluation of their antimicrobial activity (original) (raw)
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Heteroatom Chemistry, 2006
The behavior of ethyl 2-phenylthiocarbamoyl acetate 1 toward a variety of several ␣-halocarbonyl compounds was investigated. Thus, reaction of 1 with ␣-bromoketones, hydrazonoyl bromides, and 2-chloro-N-arylacetamides afforded the corresponding dihydrothiazole, 1,3,4-thiadiazole, and thiophene derivatives, respectively. The synthesis of thiazolidin-4one 11, thiazolidin-5-one 12, and some azo derivatives of thiazolidin-5-one were described. 5-Arylazothiazoles 17 and 19 were synthesized by condensation of hydrazonoyl bromides 3 with different thiourea derivatives.
Design and synthesis of some new thiophene and 1,3,4-thiadiazole based heterocycles
Phosphorus, Sulfur, and Silicon and the Related Elements, 2019
The reaction of 3-oxopropanenitriles with phenyl isothiocyanate in DMF containing KOH afforded the corresponding potassium salts. The latter salts were converted into ketene N,S-acetals upon acidification with hydrogen chloride. The reaction of the ketene N,S-acetals with 2-bromo-1-[5methyl-1-(p-tolyl)-1H-1,2,3-triazol-4-yl]ethan-1-one or 3-(2-bromoacetyl)-2H-chromen-2-one gave novel thiophenes in good yields. Treatment of the ketene N,S-acetals with hydrazonyl halides afforded 1,3,4-thiadiazoles in good yields. The stereochemistry of the synthesized compounds was studied.
International Journal of Scientific Research in Science and Technology, 2020
Thiazole represents important class of heterocyclic compounds. Thiazole and its derivatives have been reported to possess antitubercular, antibacterial, anti-inflammatory, anticancer, antifungal activity. Several methods of synthesis of thiazole derivatives have been reported, but most widely used synthetic approach to obtained thiazole derivatives is Hantzsch process. It involved synthesis of thiazole derivative from ?-halo-carbonyl compounds and thiourea or thiourea derivatives. This review mainly focuses on the research work reported in the scientific literature on the different procedures of synthesis of 2-amino thiazole and their derivatives.
Journal of Heterocyclic Chemistry, 2020
We reported here reactions of 2‐bromo‐1‐(4‐methyl‐2‐(tosylamino)thiazol‐5‐yl)ethanone 1 with 2‐cyanoethanethioamide afforded new 2‐cyanomethylthiazole derivative. The reaction of the latter with arylidenemalononitrile derivatives afforded thiazolo[3,2‐a]pyridine derivatives. Also, compound 1 was subjected to a one‐pot four component Gewald reaction with molecular sulfur, malononitrile and aromatic aldehydes in the presence of L‐proline afforded 2‐aminothiophene derivatives. The structure of the newly synthesized compounds was established based on its elemental and spectral data.
Facile synthesis of novel polysubstituted thiopene and 1,3,4-thiadiazole derivatives
Tetrahedron, 1997
3-(Benzothia7ol-2-yl)-.i-oxoDropanenitriic (1) reacts with phenylisothiocyanatc in the prcw~c ol potassium hydroxide followed by addition of the hydrazonoyl bromides 2a-c to afford the novel I .X4thiadiazole derivatives 6a-c via the intermediate 4. Reaction of 4 with 2.hromoacetylhenzothia/olc (3) furnished the new polysuhstituted thiophene 13. Treatment of the latter product with aromatic dia/onium salts resulted in the formation of 2.arylazothiophene derivatives 16a-c. A su,,-eqtcd mechanism\ of the investqated reactions were presented. Copyright 0 1996 Elsevier Science Ltd In continuation of our studies on the chemistry of 3-(benzothiazol-2-yl)-3-oxopropanenitrile (1). ' ,* N-aryla-oxo-2-benzothiazoleethanehydrazonoyl bromides 2a-c2p3 and 2-bromoacetylbenzothiazole (3).3 and as part of our program directed towards developing new approaches to a variety of heterocycles incorporating benzothiazole moiety lms of expected potential biological activity, we report here on the utility of the highly versatile, multifunctional intermediates 1,2, and 3 as building blocks for the synthesis of the title compounds.
Synthetic access to some new benzothiazole-based 1,3,4-thiadiazole and 1,3-thiazole derivatives
TURKISH JOURNAL OF CHEMISTRY, 2016
1-(Benzothiazol-2-yl)-3-phenylthiourea 2 was prepared and treated with hydrazonoyl chlorides 3a-e to yield the corresponding 5-(benzothiazol-2-ylimino)-1,3,4-thiadiazole derivatives 6a-e, respectively. Reaction of the thiourea derivative 2 with ethyl 2-chloro-3-oxobutanoate 9 afforded the corresponding 2-(benzothiazol-2-ylimino)thiazole-5-carboxylate derivative 11. The newly synthesized heterocyclic derivatives were confirmed from their elemental and spectral analyses.
Studies on the synthesis and bioactivity of some thiadiazole derivatives
1999
Several 2-aryl-3-(4-aryl-1 ,3 ,4-thiadiazolyl)-4-thiazolidinones 3 and several ot her fused heterocycles 5 have been prepared. Most of the compounds 3 have been screened for th ier fungicidal activity against two fungi Aspergillus claVa/ US and Aspergillus j UllligotllS and bacterici dal activity against Klebsilla species, and found to be active agai nst these microorgani sms .
HETEROCYCLES, 2016
A novel series of 2-ethylidenehydrazono-5-arylazothiazoles 5a-h and 2-ethylidenehydrazono-5-arylazothiazolones 9a-d were prepared by cyclocondensation of hydrazonyl halides 3a-h and 7a-d with ethylidenethiosemicarbazide 2. In addition, reaction of 2 with N-phenylcarbohydrazonyl chloride (14), afforded 1,3,4-thiadiazole derivative 17 as the end product. Moreover, the thiosemicarbazide derivative 2 was reacted with various bromoacetyl compounds 19a-d and 1,1'-(1,4-phenylene)bis(2-bromoethanone) (21) furnished the respective thiazole derivatives 20a-d and 1,4-phenylene-bisthiazole derivative 22. The structures of the newly synthesized compounds were established on the basis of spectroscopic evidences and their alternative syntheses. The newly synthesized compounds were evaluated for their antitumor activities against hepatocellular carcinoma (HepG2) cell line and the results revealed promising activities of compounds 5h, 5d, 5g, 5f and 5e with IC50 equal 2.23 ± 0.28, 2.48 ± 0.34, 2.49 ± 0.24, 4.03 ± 0.11, and 5.32 ± 0.27 μM, respectively. Functionalized thiazole derivatives have received much attention due to their diverse biological activities such as antimicrobial, 1 antiviral, 2 cytotoxic and antitumor, 3-6 and HIV-protease inhibitory agents. 7 Compounds incorporating two thiazole rings either directly connected as in bisthiazoles or through a linker unit as in bisthiazolyl compounds, show pronounced biological activity as DNA replication inhibitors in the tumor cells 8 and HIV-protease inhibitors. 7-9 Pyridine deivatives also play a key role catalyzing both biological and chemical systems. In many enzymes of living organisms it is the prosthetic pyridine nucleotide (NADP) that is involved in various 954
Synthesis and Reactions of Some Thiazole Derivatives
A series of novel 2-aminothiazole derivatives (3a-e) has been synthesized by the reaction of 4-[4methoxy-3-methylphenyl]-4-oxobutenoic acid (1) with thiourea derivatives (2a-e). The thiazolopyridazine derivatives (4a-c) and (5) were obtained from the reaction of 4-hydroxy-1,3-thiazole (3a-e) with hydrazine and phenylhydrazine, respectively. The behavior of the 4-hydroxy-1,3-thiazole (3a-e) toward acetic anhydride and bromine was also studied. The proposed structures of the products were based on microanalytical and spectroscopic data.