Category: thiazole

Stereoselective formation of (Z)-2-fluoroalkenoates via Julia-Kocienski reaction of aldehydes with pyrimidinyl-fluoro-sulfones was written by Larnaud, Florent;Pfund, Emmanuel;Linclau, Bruno;Lequeux, Thierry. And the article was included in Tetrahedron in 2014.Name: 5-Nitrobenzothiazole-2-thiol This article mentions the following:

The selective synthesis of fluoroalkenoates is reported using a pyrimidine-fluoro-sulfone as a starting material. This sulfone allowed the preparation of (Z)-fluoroalkenoates with very high stereoselectivity from both aromatic and aliphatic aldehydes. The nature of the heterocycle on the course of the Julia-Kocienski reaction is discussed. A Julia-Kocienski reaction involves the formation of alkenes by a reaction of sulfones with aldehyde derivatives In this work the synthesis of the target compounds was achieved using 4-bromobenzaldehyde, 2,5-dibromobenzaldehyde, 2-thiophenecarboxaldehyde, 2-furancarboxaldehyde, heptanal, nonanal, 10-undecanal, (S)-citronellal, benzenepropanal, cyclohexanecarboxaldehyde, (1S,3R)-3-formyl-2,2-dimethylcyclopropanecarboxylic acid ester as aldehyde components. Sulfone components contained a fluorine group, such as 2-[(2-benzothiazolyl)sulfonyl]-2-(fluoro)acetic acid Et ester, 2-fluoro-2-[(2-pyridinyl)sulfonyl]acetic acid Et ester, 2-fluoro-2-[(2-pyrimidinyl)sulfonyl]acetic acid Et ester. The title compounds thus formed included (2Z)-3-(4-bromophenyl)-2-fluoro-2-propenoic acid ester, (2Z)-2-fluoro-3-(2-thienyl)-2-propenoic acid ester, (2Z)-2-fluoro-3-(2-furanyl)-2-propenoic acid ester, (2Z)-2-fluoro-2-nonenoic acid ester, (1S,3S)-3-[(1Z)-3-ethoxy-2-fluoro-3-oxo-1-propen-1-yl]-2,2-dimethylcyclopropanecarboxylic acid ester. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0Name: 5-Nitrobenzothiazole-2-thiol).

5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.Name: 5-Nitrobenzothiazole-2-thiol

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Gold nanoparticle catalyzed intramolecular C-S bond formation/C-H bond functionalization/cyclization cascades was written by Gogoi, Prasanta;Paul, Bappi;Hazarika, Sukanya;Barman, Pranjit. And the article was included in RSC Advances in 2015.Reference of 1843-21-6 This article mentions the following:

An efficient synthesis of 2-(N-aryl)aminobenzo[d]-1,3-thiazoles via intramol. C-S bond formation/C-H bond functionalization utilizing an unusual cocatalytic Au-NPs/KMnO₄ system under an oxygen atm. at 80° was presented. Au-NPs could be easily prepared by using HAuCl₄ with reductive potential of Kayea assamica (sia nahor) aqueous fruit extract The catalyst could be easily separated and recycled eight times without any appreciable loss of activity. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Reference of 1843-21-6).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. Electrophilic attack at nitrogen depends on the presence of electron density at nitrogen as well as the position and nature of substituent linked to the thiazole ring.Reference of 1843-21-6

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

A New, Efficient and Recyclable Lanthanum(III) Oxide- Catalyzed C-N Cross-Coupling was written by Murthy, S. Narayana;Madhav, B.;Reddy, V. Prakash;Nageswar, Y. V. D.. And the article was included in Advanced Synthesis & Catalysis in 2010.Recommanded Product: 1843-21-6 This article mentions the following:

A new and efficient protocol for the C-N cross-coupling of aryl halides with heteroaromatic amines using lanthanum(III) oxide (10 mol%) as a recyclable catalyst, N,N’-dimethylethylenediamine (DMEDA) (20 mol%)as a ligand, and potassium hydroxide (KOH) as a base in DMSO at 110 °C has been developed. This inexpensive catalytic system is highly effective towards the amination of aryl halides with various nitrogen nucleophiles and is significantly tolerant towards other functional groups in the substrates. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Recommanded Product: 1843-21-6).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. Electrophilic attack at nitrogen depends on the presence of electron density at nitrogen as well as the position and nature of substituent linked to the thiazole ring.Recommanded Product: 1843-21-6

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Synthesis and antimitotic activity of 3- and 5-halo-substituted bis(2-aminophenyl) disulfides and corresponding N-alkyl derivatives was written by Mazzone, G.;Pappalardo, G.. And the article was included in Farmaco, Edizione Scientifica in 1977.Computed Properties of C7H4ClNOS This article mentions the following:

Benzothiazolones I (R = H, alkyl, CH2CO2Et; R1 or R2 = H, the other is Cl or F) were heated with NaOH to yield eleven resp. diphenyl disulfides II (R3 = H, alkyl, CH2CO2H). Antimitotic activity was found for II (R1 = H, R2 = Cl, R3 = Me) and II (R1 = H, R2 = F, R3 = Me). In the experiment, the researchers used many compounds, for example, 6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3Computed Properties of C7H4ClNOS).

6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3) belongs to thiazole derivatives. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.Computed Properties of C7H4ClNOS

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Differences in chemical constituents of poplar varieties with different anti-rust resistances was written by Zhu, Jingfang;Zhou, Yongbin. And the article was included in Dongbei Linye Daxue Xuebao in 2012.Name: 5-Phenylthiazole This article mentions the following:

An experiment was conducted to study the differences in fat soluble constituents in six poplar clones with different antirust resistances by ultrasonic extraction technique with petroleum ether and GC-MS anal. in order to shorten the breeding time. The six poplar clones were I108, 03-04-170, 03-04-141, 03-04-111, N177 and N195. Results show that the differences in fat soluble constituents are significant in the buds of poplar with different anti-rust resistances. The buds of N195 and N177 which resist poplar rust well contain such endemic elements as α-Caryophyllene, α-Bisabolol, and Me arachidate. Cinnamic acid, 4-Cyanophenyl-propylbenzoate, 9-Phenanthrol, Chlorodiphenylmethane, retinaldehyde, and p-Hydroxy-cinnamic acid only exist in N195, while α-cadinol, 2-Phenethyl octanoate, 9-Aminoacridine, and 1-Docosanol only exist in N177. Therefore, the differences in fat soluble constituents in poplar buds may determine the rust resistance in poplar. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Name: 5-Phenylthiazole).

5-Phenylthiazole (cas: 1826-13-7) belongs to thiazole derivatives. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.Name: 5-Phenylthiazole

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Synthesis and structure-activity relationship of aminoarylthiazole derivatives as correctors of the chloride transport defect in cystic fibrosis was written by Pesce, Emanuela;Bellotti, Marta;Liessi, Nara;Guariento, Sara;Damonte, Gianluca;Cichero, Elena;Galatini, Andrea;Salis, Annalisa;Gianotti, Ambra;Pedemonte, Nicoletta;Zegarra-Moran, Olga;Fossa, Paola;Galietta, Luis J. V.;Millo, Enrico. And the article was included in European Journal of Medicinal Chemistry in 2015.Name: 6-Bromo-2-chlorobenzothiazole This article mentions the following:

(Arylamino)arylthiazoles such as I were prepared and tested for their ability to correct mutations in the folding and function of the cystic fibrosis transmembrane conductance regulator (CFTR) and to determine general structure-activity relationships for correcting folding (processing) mutations and functional mutations (potentiation) of the CFTR. I acted as both a corrector and potentiator for the CTFR; its efficacy was improved and marked synergy was present when used in combination with the corrector VX-809. Mol. docking of I and two other (arylamino)arylthiazoles to the nucleotide binding domain NBD1 of the CFTR was performed to determine their binding sites to the CTFR. In the experiment, the researchers used many compounds, for example, 6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4Name: 6-Bromo-2-chlorobenzothiazole).

6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.Name: 6-Bromo-2-chlorobenzothiazole

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Catalyst-dependent chemoselective insertion of diazoalkanes into the N-H/C-H/O-H/C-O bonds of 2-hydroxybenzothiazoles was written by Jin, Lvnan;Zhou, Xuan;Zhao, Yunbo;Guo, Jing;Stephan, Douglas W.. And the article was included in Organic & Biomolecular Chemistry in 2022.Electric Literature of C7H4ClNOS This article mentions the following:

The chemoselective N-H, O-H, C-O or C-H bond insertions of diazoalkanes into 2-hydroxybenzothiazoles were achieved using B(C₆F₅)₃, Rh₂(OAc)₄ or TfOH as the catalyst. This afforded routes to 54 benzothiazole derivatives These protocols are scalable and demonstrate the complementary nature of Lewis acid, transition metal and Bronsted acid catalyzes. In the experiment, the researchers used many compounds, for example, 6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3Electric Literature of C7H4ClNOS).

6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.Electric Literature of C7H4ClNOS

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Low energy excited singlet states of some monophenyl substituted 5-membered heterocycles and their photoisomerization was written by Mehlhorn, A.;Fratev, F.;Monev, V.. And the article was included in Tetrahedron in 1981.Application In Synthesis of 5-Phenylthiazole This article mentions the following:

The 2 low-lying singlet excited states of 14 monophenylated 5-membered heterocycles were studied with respect to their energy level ordering, the oscillator strengths of the pertinent transitions, the state wave functions, and the 1-particle d. matrixes. Two types of lowest energy singlet states were found by configuration anal. and similarity anal. One state is characterized by delocalization over the whole π system, whereas the other is locally excited at the Ph moiety. The relation between this classification and the different photoisomerization paths of the title compounds is discussed. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Application In Synthesis of 5-Phenylthiazole).

5-Phenylthiazole (cas: 1826-13-7) belongs to thiazole derivatives. The thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Application In Synthesis of 5-Phenylthiazole

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Small molecules enhance functional O-mannosylation of Alpha-dystroglycan was written by Lv, Fengping;Li, Zhi-fang;Hu, Wenhao;Wu, Xiaohua. And the article was included in Bioorganic & Medicinal Chemistry in 2015.Reference of 58759-63-0 This article mentions the following:

Alpha-dystroglycan (α-DG), a highly glycosylated receptor for extracellular matrix proteins, plays a critical role in many biol. processes. Hypoglycosylation of α-DG results in various types of muscular dystrophies and is also highly associated with progression of majority of cancers. Currently, there are no effective treatments for those devastating diseases. Enhancing functional O-mannosyl glycans (FOG) of α-DG on the cell surfaces is a potential approach to address this unmet challenge. Based on the hypothesis that the cells can up-regulate FOG of α-DG in response to certain chem. stimuli, the authors developed a cell-based high-throughput screening (HTS) platform for searching chem. enhancers of FOG of α-DG from a large chem. library with 364,168 compounds Sequential validation of the hits from a primary screening campaign and chem. works led to identification of a cluster of compounds that pos. modulate FOG of α-DG on various cell surfaces including patient-derived myoblasts. These compounds enhance FOG of α-DG by almost ten folds, which provide us powerful tools for O-mannosylation studies and potential starting points for the development of drug to treat dystroglycanopathy. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0Reference of 58759-63-0).

5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0) belongs to thiazole derivatives. Thiazoles frequently appear in peptide studies. Thiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis. The nitrogen in thiazole is sp2 hybridized and the lone pair of electrons localized on the nitrogen is less reactive due to increased aromatic character and decreased basicity. It is protonated and alkylated/acylated at nitrogen forming hydrochloride and quaternary thiazolium salt.Reference of 58759-63-0

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Experimental and theoretical study of the reactivity of thiazole and 4,5-dimethylthiazole towards free phenyl and substituted phenyl radicals was written by Vitry-Raymond, Jacqueline;Metzger, Jacques. And the article was included in Bulletin de la Societe Chimique de France in 1963.Synthetic Route of C9H7NS This article mentions the following:

The reactivity of thiazole (I) towards free phenyl and p-nitrophenyl radicals (obtained by the thermal decomposition of Bz₂O₂ and p-nitrophenyldiazonium salts, resp.) was investigated. The results are interpreted on the basis of the radical polarization energies calculated by the mol. orbital method. I and Bz₂O₂ in a molar ratio of 55:1 heated at 80° under N, excess I removed, the residue hydrolyzed, and the mixture steam distilled gave a mixture of 52% 2- (II), 37% 5- (III), and 11% 4-phenylthiazole (IV). The crude residue from a similar run extracted with C₆H₆, the extract successively reextracted with concentrated HCl and concentrated aqueous NaOH, the acidic extract neutralized and extracted with Et₂O, and the extract evaporated yielded 8% mixture of 54-6% II, 29-31% III, and 13-17% IV; the alk. extract neutralized gave BzOH, m. 122°, and p-PhC₆H₄CO₂H, m. 114°. These results show that the steam distillation apparently caused a reduction of the yields of IV and that in all runs the decreasing order of reactivity of the various positions in I was 2 > 5 > 4. The spectroscopic analysis of the steam-distilled product showed the presence of 60% II, 24% III, and 16% IV. I treated with p-nitrodiazonium salts under the conditions described previously for the reaction with 4,5-dimethylthiazole (CA 55, 22288c) gave 14% of a mixture of 3 isomeric monosubstitution products. The electron distribution in 2-, 4-, and 5-methylthiazole and in 4,5-dimethylthiazole was calculated In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Synthetic Route of C9H7NS).

5-Phenylthiazole (cas: 1826-13-7) belongs to thiazole derivatives. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.Synthetic Route of C9H7NS

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica