Tag: 100-200

Bimetallic Cooperative Catalysis for Decarbonylative Heteroarylation of Carboxylic Acids via C-O/C-H Coupling was written by Liu, Chengwei;Ji, Chong-Lei;Zhou, Tongliang;Hong, Xin;Szostak, Michal. And the article was included in Angewandte Chemie, International Edition in 2021.SDS of cas: 1826-13-7 This article mentions the following:

Cooperative bimetallic catalysis is a fundamental approach in modern synthetic chem. We report bimetallic cooperative catalysis for the direct decarbonylative heteroarylation of ubiquitous carboxylic acids via acyl C-O/C-H coupling [e.g., benzoxazole + benzoic acid → 2-phenylbenzoxazole (92%)]. This novel catalytic system exploits the cooperative action of a copper catalyst and a palladium catalyst in decarbonylation, which enables highly chemoselective synthesis of important heterobiaryl motifs through the coupling of carboxylic acids with heteroarenes in the absence of prefunctionalization or directing groups. This cooperative decarbonylative method uses common carboxylic acids and shows a remarkably broad substrate scope (>70 examples), including late-stage modification of pharmaceuticals and streamlined synthesis of bioactive agents. Extensive mechanistic and computational studies were conducted to gain insight into the mechanism of the reaction. The key step involves intersection of the two catalytic cycles via transmetalation of the copper-aryl species with the palladium(II) intermediate generated by oxidative addition/decarbonylation. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7SDS of cas: 1826-13-7).

5-Phenylthiazole (cas: 1826-13-7) belongs to thiazole derivatives. Thiazoles in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.SDS of cas: 1826-13-7

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

Novel pyrazinone mono-amides as potent and reversible caspase-3 inhibitors was written by Han, Yongxin;Giroux, Andre;Colucci, John;Bayly, Christopher I.;Mckay, Daniel J.;Roy, Sophie;Xanthoudakis, Steve;Vaillancourt, John;Rasper, Dita M.;Tam, John;Tawa, Paul;Nicholson, Donald W.;Zamboni, Robert J.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2005.COA of Formula: C4H6N2S This article mentions the following:

The iterative process for the discovery of a series of pyrazinone mono-amides as potent, selective and reversible non-peptide caspase-3 inhibitors (e.g., M826 and M867) is reported. The studied compounds were prepared according to modified literature procedure from ethylaminobutyrate hydrochloride via intermediate acids (e. g., I), which were synthesized using Dess-Martin periodinane oxidation Treating of coupled to the resin in the presence of Hunig’s base intermediate acids I with 90% TFA in water gave the desired inhibitors (e. g. II). These compounds were screened directly, without further purification, against four representative recombinant human caspases, as well as in the NT2 cell against camptothecin induced apoptosis. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1COA of Formula: C4H6N2S).

Thiazol-2-ylmethanamine (cas: 55661-33-1) 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. 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.COA of Formula: C4H6N2S

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

Carbon-13 NMR studies of variously substituted phenylthiazoles. Substituent effects, conformational study and prototropic tautomerism was written by Faure, Robert;Assaf, Abdelghani;Vincent, Emile Jean;Aune, Jean Pierre. And the article was included in Journal de Chimie Physique et de Physico-Chimie Biologique in 1978.Synthetic Route of C9H7NS This article mentions the following:

The ¹³C NMR of I (R = H, 2-Ph, 4-Ph, 5-Ph) was examined and the dihedral angle between the Ph and thiazole ring systems determined; comparison of other heterocyclic ring systems with I indicated that the perturbation observed on Ph substitution decreased with the increase in heteroatom electronegativity. Steric interactions were observed in 4,5-disubstituted phenylthiazoles and the substituent effects were nonadditive; additivity was observed in 2,4- and 2,5-disubstituted phenylthiazoles. The protonation of I and the tautomerization of II (R¹ = H, Ph; R² = NH₂, SH, OH) was also discussed. 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 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. 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.Synthetic Route of C9H7NS

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

Some thiazoles and oxazoles was written by Bachstez, Marcel. And the article was included in Berichte der Deutschen Chemischen Gesellschaft in 1914.Reference of 1826-13-7 This article mentions the following:

Rüdenburg, C. A. 8, 686. From 2 g. each of BzNHCH₂CH(OEt)₂ and P₂S₅, heated on the H₂O bath till the foaming ceases, is obtained 0.3 g. 2-phenylthiazole (Hubacher, Ann. 269, 234) . 1 g. HCONHCH₂Bz (a), m. 81-2° (Pictet and Gams, C. A. 4, 3222, give 70-1°), heated 10 min. with 1.5 g. P₂S₅, gives 0.6 g. 5-phenylthiazole, iridescent leaflets, m. 45-6°; hydrochloride, hygroscopic needles, decompose by much H₂O or by warming; chloroplatinate, yellow precipitate, decompose 281-2°; chloroaurate, yellow-red rhombic plates, sinters 170°, m. 185°, decompose about 223°; chromate, ocher-yellow rodlets and needles from 10% HCl, m. 108-9° (decompose); picrate, light yellow needles, m. 138-9° (decompose). 5-Phenyloxazole, from (a) and PCl₅ after 10 min. on the H₂O bath, m. 41-2°; hydrochloride, hygroscopic; chloroaurate, long orange needles, m. 149-50°; chloroplatinate, long light yellow needles, does not decompose 275°. α-Acetaminopropiophenone (b), obtained in 0.8 g. yield from 1 g. BzCHMeNH₂.HCl in 15 cc. ice H₂O and 2 cc. Ac₂O, rhombic pyramids from C₆H₆, m. 90-1°; with 2 parts PCl₅ 10 min. on the H₂O bath it gives 2,4-dimethyl-5-phenyloxazole, m. 51-2°; hydrochloride, hygroscopic rodlets, slowly volatilizes in vacuo, decompose by H₂O; chromate, orange needles, m. 100-1° (foaming); chloroplatinate, long yellow-red needles with 2 H₂O, m. 240° (foaming); chloroaurate, short rodlets; picrate, felted needles, m. 171-2.5°. 2,4-Dimethyl-5-phenylthiazole, obtained in 50% yield from equal parts of (b) and P₂S₄ heated 10 min. to 140°, b₇₆₈ 270-1°; hydrochloride, hygroscopic rodlets, decompose by much H₂O; chloroplatinate, long yellow-red needles with 2 H₂O, sinters 235°, m. 239-40° (foaming); chloroaurate, needles; chromate, fleshred needles, m. 105-6°; picrate, felted needles, m. 155.5-6.5°. Benzaminoisobutyrophenone, from BzCMe₂NH₂.HCl and BzCl in NaOH, needles from 50% alc., m. 61°, does not react with PCl₅ alone or in POCl₃. ω-Ethyloxalylaminoacetophenone, BzCH₂NHCOCO₂Et, from BzCH₂NH₂.HCl in cold H₂O treated with NaHCO₃ and ClOCCO₂Et, striated prisms from H₂O, m. 96-7°; the yield was so small that its reaction with PCl₄ could not be tried out. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Reference of 1826-13-7).

5-Phenylthiazole (cas: 1826-13-7) 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. There are numerous natural products that possess a thiazole ring with broad pharmacological activities. Thiamine, also known as vitamin B1, possesses a thiazole ring linked with 2-methylpyrimidine-4-amine as hydrochloride salt.Reference of 1826-13-7

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

CuI-catalyzed one-pot synthesis of benzothiazolones from 2-iodoanilines-derived carbamates and sodium sulfide was written by Li, Jiaojiao;Zhang, Yihua;Jiang, Yongwen;Ma, Dawei. And the article was included in Tetrahedron Letters in 2012.Category: thiazole This article mentions the following:

A copper-catalyzed procedure was developed for assembling benzothiazolones from Et 2-iodophenylcarbamates and sodium sulfide. A number of functional groups, such as methoxy, acyl, amide, carboxylate, trifluoromethyl, fluoro, and chloro, were tolerated under these conditions, providing benzothiazolones in good yields. In the experiment, the researchers used many compounds, for example, 6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3Category: thiazole).

6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3) 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. There are numerous natural products that possess a thiazole ring with broad pharmacological activities. Thiamine, also known as vitamin B1, possesses a thiazole ring linked with 2-methylpyrimidine-4-amine as hydrochloride salt.Category: thiazole

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

Ligand-Promoted Alkynylation of Aryl Ketones: A Practical Tool for Structural Diversity in Drugs and Natural Products was written by Xu, Hui;Ma, Biao;Fu, Zunyun;Li, Han-Yuan;Wang, Xing;Wang, Zhen-Yu;Li, Ling-Jun;Cheng, Tai-Jin;Zheng, Mingyue;Dai, Hui-Xiong. And the article was included in ACS Catalysis in 2021.Name: Benzothiazole-5-carboxylic acid This article mentions the following:

A palladium-catalyzed ligand-promoted alkynation of unstrained aryl ketones RC(O)R¹ (R = naphthalen-2-yl, 1-benzothiophen-5-yl, 4-(2H-1,2,3-triazol-2-yl)benzen-1-yl, etc.; R¹ = Me, n-Pr, Ph, etc.) have been reported. The protocol allows the alkynation to be carried out in a one-pot procedure with broad functional-group tolerance and substrate scope for the synthesis of aryl-/terminal alkynes RCCR² (R² = 2-fluorophenyl, naphthalen-2-yl, thiophen-2-yl, etc.) and RCCH. The potential applications of this protocol in drug discovery and chem. biol. are further demonstrated by late-stage diversification of a number of pharmaceuticals and natural products e.g., I. More importantly, two different biol. important fragments R³CCR⁴ (R = 3-methoxy-4-([(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy)benzen-1-yl, 6-[3-(adamantan-1-yl)-4-methoxyphenyl]naphthalen-2-yl; R⁴ = 4-(dipropylsulfamoyl)phenyl) derived from a pharmaceutical and natural product could be connected by the consecutive alkynation of ketones CH₃(CH₂)₂C(O)R⁴. Distinct from aryl halides in conventional Sonogashira reactions, the protocol provides a practical tool for the 1,2-bifunctionalization of aryl ketone (1-[(17β)-17-(acetyloxy)estra-1,3,5(10)-trien-2-yl]ethanone) by merging ketone-directed ortho-C-H activation with ligand-promoted ipso-Ar-C(O) alkynation. In the experiment, the researchers used many compounds, for example, Benzothiazole-5-carboxylic acid (cas: 68867-17-4Name: Benzothiazole-5-carboxylic acid).

Benzothiazole-5-carboxylic acid (cas: 68867-17-4) 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. 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: Benzothiazole-5-carboxylic acid

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

Synthesis and structure-activity relationships of amide derivatives of (4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepin-5-ylidene)acetic acid as selective arginine vasopressin V₂ receptor agonists was written by Tsukamoto, Issei;Koshio, Hiroyuki;Kuramochi, Takahiro;Saitoh, Chikashi;Yanai-Inamura, Hiroko;Kitada-Nozawa, Chika;Yamamoto, Eisaku;Yatsu, Takeyuki;Shimada, Yoshiaki;Sakamoto, Shuichi;Tsukamoto, Shin-ichi. And the article was included in Bioorganic & Medicinal Chemistry in 2009.Related Products of 55661-33-1 This article mentions the following:

A series of (4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepin-5-ylidene)acetamide derivatives was synthesized, and their structure-activity relationships were examined in order to identify potent and selective arginine vasopressin V₂ receptor agonists. Attempts to substitute other chem. groups in place of the 2-pyridilmethyl moiety of 1a led to the discovery that potent V₂ binding affinity could be obtained with a wide range of functional groups. This structural tolerance allowed for the manipulation of other attributes, such as selectivity against V_1a receptor affinity or avoidance of the undesirable inhibition of cytochrome P 450 (CYP), without losing potent affinity for the V₂ receptor. Some representative compounds obtained in this study were also found to decrease urine volume in awake rats. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Related Products of 55661-33-1).

Thiazol-2-ylmethanamine (cas: 55661-33-1) 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. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Related Products of 55661-33-1

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

AM1 molecular orbital study of the transmission of electronic effects in the 5-membered heteroaromatics: proton and hydride ion affinities of 4- and 5-substituted (2-heteroaromatic)methyl anions and cations was written by Bean, Gerritt P.. And the article was included in Journal of Organic Chemistry in 1993.HPLC of Formula: 89281-44-7 This article mentions the following:

The proton and hydride ion affinities of a series of the benzyl-like anions and cations of 4- and 5-substituted 2-Me 5-membered heteroaromatic compounds have been calculated by the AM1 MO method. Calculations included para- and meta-substituted toluenes, similarly substituted 1,3-pentadienes, and 3-aza-1,3-pentadienes as various models for the possible pathways for the effect of the substituents to be transmitted to the reaction site. There was excellent correlation between the 4-substituted compounds and the m-toluenes and between the 5-substituted compounds and the p-toluenes. Compared to the other ring atoms, substituents at either the 4- or 5-position have little effect on the change in the charges on the heteroatoms in going to either the cation or anion of the heteroaromatic compounds Transmission of electronic effects is primarily through the carbon skeleton with little if any through the heteroatom. In the experiment, the researchers used many compounds, for example, 2-Methylthiazol-5-amine (cas: 89281-44-7HPLC of Formula: 89281-44-7).

2-Methylthiazol-5-amine (cas: 89281-44-7) 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 sulfonation occurs only under forcing conditions: the action of oleum at 250 °C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.HPLC of Formula: 89281-44-7

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

From dihydroxypyrimidine carboxylic acids to carboxamide HIV-1 integrase inhibitors: SAR around the amide moiety was written by Petrocchi, Alessia;Koch, Uwe;Matassa, Victor G.;Pacini, Barbara;Stillmock, Kara A.;Summa, Vincenzo. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2007.Quality Control of Thiazol-2-ylmethanamine This article mentions the following:

4,5-Dihydroxypyrimidine carboxamides, which evolved from a related series of HCV NS5b polymerase inhibitors, have been optimized to provide selective HIV integrase strand transfer inhibitors. Extensive SAR around the benzylamide moiety led to the identification of the p-fluorobenzylamide compound I as optimal in the enzymic assay. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Quality Control of Thiazol-2-ylmethanamine).

Thiazol-2-ylmethanamine (cas: 55661-33-1) belongs to thiazole derivatives. Thiazoles in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications. 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.Quality Control of Thiazol-2-ylmethanamine

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

Electronic spectra of benzothiazolone and its derivatives was written by Simov, D.;Antonova, A.. And the article was included in Godishnik na Sofiiskiya Universitet Sv. Kliment Okhridski, Khimicheski Fakultet in 1976.HPLC of Formula: 62266-81-3 This article mentions the following:

UV spectra are tabulated for benzothiazolones I (R = H, 3-Me, 6-Me, 5-MeO, 6-MeO, 5-Cl, 6-Cl, 6-Br, 5-Me2NSO2, 6-Me2NSO2, 5-NO2, 6-NO2) in 20% solution in EtOH and in H2O at pH 0.5, 7 and 11.5. The peaks for I (R = H, Me) came at lower wavelengths than those for the other I. In the experiment, the researchers used many compounds, for example, 6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3HPLC of Formula: 62266-81-3).

6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at δ 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. 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.HPLC of Formula: 62266-81-3

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