Tag: M.W=200-250

Kadam, Shuddhodan N.; Ambhore, Ajay N.; Hebade, Madhav J.; Kamble, Rahul D.; Hese, Shrikant V.; Gaikwad, Milind V.; Gavhane, Priya D.; Dawane, Bhaskar S. published the artcile< Metal-Free One-Pot Chemoselective Thiocyanation of Imidazothiazoles and 2-Aminothiazoles with in situ Generated N-Thiocyanatosuccinimide>, Formula: C9H7N3O2S, the main research area is thiocyanoimidazothiazole thiocyanoaminothiazole preparation green chem; imidazothiazole aminothiazole metal free chemoselective thiocyanation.

A chemoselective thiocyanation of imidazothiazoles and 2-aminothiazoles with use of in situ generated N-thiocyanatosuccinimide (NTS) at room temperature is described. The protocol offers mild reaction conditions and high chemoselectivity for electrophilic substitution in imidazothiazoles over nucleophilic substitution. This method provides metal-free and easy conversion of imidazothiazoles and 2-aminothiazoles into their corresponding C-3 and C-5 thiocyanates, resp., in good to excellent yield. The present protocol also offers the effective thiocyanation of bifunctional imidazothiazoles containing aliphatic -OH and C(sp2)-H bond functionalities.

Synlett published new progress about Chemoselectivity. 57493-24-0 belongs to class thiazole, and the molecular formula is C9H7N3O2S, Formula: C9H7N3O2S.

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

Wu, Yikang; Shen, Xin; Yang, Yong-Qing; Hu, Qi; Huang, Jia-Hui published the artcile< Enantioselective Total Synthesis of (+)-Brefeldin A and 7-epi-Brefeldin A>, Category: thiazole, the main research area is asym synthesis brefeldin a epibrefeldin stereoselective aldol chiral auxiliary; chiral auxiliary oxazolidinone thiazolidinethione stereoselective aldol reaction protecting group; stereoselective reduction elimination solvent effect asym synthesis brefeldin a; intramol Mukaiyama aldol condensation stereoselective Michael asym synthesis brefeldin.

A convergent enantioselective route to brefeldin A (I) and 7-epi-BFA was developed. The key C-4/C-5 chiral centers were established by using chiral auxiliary induced intermol. asym. aldolization in the presence of TiCl4 and TMEDA. The results with the thiazolidinethione/TiCl4 mediated intermol. asym. aldolization added some new information about the scope and limitations to the existing knowledge of that type of reactions (which so far was essentially limited to the reactions with N-propionyl thiazolidinethiones). During the course a method for protecting the liable aldol hydroxyl groups by using inexpensive TBSCl in DMF with 2,6-lutidine as the base was developed to replace the otherwise unavoidable TBSOTf procedure. Due to the excessive steric hindrance, removal of the auxiliary was much more difficult than most literature cases. Cleavage of the oxazolidinone by reduction was almost impossible. The thiazolidinethione auxiliary was relatively easier to remove. However, several reactions reported for facile removal of thiazolidinethione auxiliaries in the literature still failed. Reductive removal of the thiazolidinethione auxiliary was most effectively realized with LiBH4 in di-Et ether in the presence of 1 equiv of MeOH (a modification of a literature procedure for removal of oxazolidinone auxiliaries in less hindered substrates). Apart from the auxiliary removal, oxidation of the alc. into aldehyde and the deprotection of the dithiolane protecting group were also rather difficult in the present context. A range of methods were screened before final solutions were found. The five-membered ring was constructed by employing an intramol. Mukaiyama reaction after many attempts with the intramol. aldolization under a variety of conditions failed. The rate of elimination of the alkoxyl to form the α,β-double bond of a key intermediate cyclopentenone with DBU was highly solvent dependent (very sluggish in CH2Cl2 but rather fast in MeOH). Introduction of the lower chain (which was synthesized by using a Jacobsen KHR to establish the C-15 chirality) was achieved through a Michael addition similar to the precedents in the literature. It has not been noticed before that the yield of this Michael reaction could be dramatically raised by using 3 equiv of the copper-lithium reagent. Reduction of the C-7 carbonyl was apparently more difficult than similar cases in the literature. After examination of many reagents under various conditions, it was found that the best reagent for yielding the α-isomer was (S)-2-methyl-CBS-borolidine/BH3 and that for the β-isomer was L-Selectride. The α- and β-isomers were then further elaborated into (+)-brefeldin A and 7-epi-BFA, resp. An unexpected yet very interesting solubility difference between BFA and 7-epi-BFA was also observed

Journal of Organic Chemistry published new progress about Aldol condensation, stereoselective. 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, Category: thiazole.

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

Evans, David A.; Downey, C. Wade; Shaw, Jared T.; Tedrow, Jason S. published the artcile< Magnesium Halide-Catalyzed Anti-Aldol Reactions of Chiral N-Acylthiazolidinethiones>, Category: thiazole, the main research area is acylthiazolidinethione aldehyde anti aldol condensation; aldol condensation catalyst magnesium halide; alc stereoselective preparation.

Diastereoselective direct aldol reactions of chiral N-acylthiazolidinethiones occur in high yield with preference for the anti diastereomer, e.g., I. This reaction is catalyzed by 10% MgBr2·OEt2 in the presence of triethylamine and chlorotrimethylsilane. Yields range from 56 to 93% with diastereoselectivity up to 19:1 for a variety of N-acylthiazolidinethiones and unsaturated aldehydes.

Organic Letters published new progress about Alcohols Role: SPN (Synthetic Preparation), PREP (Preparation). 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, Category: thiazole.

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

Minor-Villar, Leticia; Tello-Aburto, Rodolfo; Olivo, Horacio F.; Fuentes, Aydee; Romero-Ortega, Moises published the artcile< Desulfurization-oxygenation of chiral 1,3-thiazolidine-2-thiones and 1,3-oxazolidine-2-thiones using propylene oxide and microwave irradiation>, COA of Formula: C10H11NS2, the main research area is desulfurization oxygenation chiral thiazolidinethione oxazolidinethione propylene oxide microwave; thiazolidinone preparation; oxazolidinone preparation.

An efficient method for the desulfurization-oxygenation of 1,3-thiazolidine-2-thiones and 1,3-oxazolidine-2-thiones using propylene oxide and employing microwave irradiation is described. This strategy of oxygenation of the thiocarbonyl group provides an attractive methodol. to prepare chiral 1,3-thiazolidin-2-ones and 1,3-oxazolidin-2-ones from the corresponding precursors in good yields.

Synlett published new progress about Desulfurization. 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, COA of Formula: C10H11NS2.

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

Zhou, Renwu; Zhou, Rusen; Zhang, Xianhui; Fang, Zhi; Wang, Xiaoxiang; Speight, Robert; Wang, Hongxia; Doherty, William; Cullen, Patrick J.; Ostrikov, Kostya; Bazaka, Kateryna published the artcile< High-Performance Plasma-Enabled Biorefining of Microalgae to Value-Added Products>, Safety of 2-Amino-4-(3-nitrophenyl)thiazole, the main research area is microalgae biorefining high performance plasma; biomass; biorefining; liquefaction; microalgae; plasma chemistry.

Conversion of renewable biomass by time- and energy-efficient techniques remains an important challenge. Herein, plasma catalytic liquefaction (PCL) is employed to achieve rapid liquefaction of microalgae under mild conditions. The choice of the catalyst affects both the liquefaction efficiency and the yield of products. The acid catalyst is more effective and gave a liquid yield of 73.95 wt % in 3 min, as opposed to 69.80 wt % obtained with the basic catalyst in 7 min. Analyses of the thus-formed products and the processing environment reveal that the enhanced PCL performance is linked to the rapid increase in temperature under the effect of plasma-induced elec. fields and the generation of large quantities of reactive species. Moreover, the obtained solid residue can be simply upgraded to a carbon product suitable for supercapacitor applications. Therefore, the proposed strategy may provide a new avenue for fast and comprehensive utilization of biomass under benign conditions.

ChemSusChem published new progress about Alcohols Role: IMF (Industrial Manufacture), PREP (Preparation). 57493-24-0 belongs to class thiazole, and the molecular formula is C9H7N3O2S, Safety of 2-Amino-4-(3-nitrophenyl)thiazole.

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

Oishi, Shunsuke; Saito, Susumu published the artcile< Double Molecular Recognition with Aminoorganoboron Complexes: Selective Alcoholysis of β-Dicarbonyl Derivatives>, Application In Synthesis of 171877-39-7, the main research area is mol recognition aminoorganoboron complex chemoselective regioselective alcoholysis dicarbonyl derivative.

Aminoorganoboron (AOB) complexes recognize alc. and β-dicarbonyl units, and thereby facilitate chemo- and site-selective alcoholysis of the latter. The complex activates both reaction partners. This strategy enables C-C, C-N, and C-O bond cleavage in addition/elimination reactions under near neutral pH conditions and provides a new method for functional group conversions.

Angewandte Chemie, International Edition published new progress about 1,3-Dicarbonyl compounds Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, Application In Synthesis of 171877-39-7.

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

Abe, Hideki; Hikichi, Takuma; Emori, Kosuke; Yokosuka, Akihito; Mimaki, Yoshihiro; Kobayashi, Toyoharu; Ito, Hisanaka published the artcile< Total Synthesis of Catunaregin and Preliminary Evaluation of Its Antitumor Activity>, Reference of 171877-39-7, the main research area is catunaregin synthesis antitumor.

The total synthesis of catunaregin in both racemic and optically active forms was accomplished. The enantioselective synthesis uses the Evans aldol strategy, with an oxazolidinone or thiazolidinethione as the chiral auxiliary. The key features include a syn-selective aldol reaction to form the Evans-syn or non-Evans-syn product, and a successive ketalization reaction of a furanyl diol derivative under acidic conditions. The biol. properties of the synthetic racemate and both enantiomers were evaluated against A549 and HL-60 human cancer cells.

European Journal of Organic Chemistry published new progress about Aldol addition, stereoselective. 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, Reference of 171877-39-7.

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

Nagase, Hiroshi published the artcile< Fungicides. XXVI. Addition of 2,3-dimethylbutadiene to 5-methoxycarbonylmethylidene-2-thioxo-4-thiazolidones and 5-aroylmethylidene-2-thioxo-4-thiazolidones>, Name: 3-Benzyl-2-thioxothiazolidin-4-one, the main research area is thiazolidonespirocyclohexene thioxo; spirothiazolecyclohexenone thioxo; thiazolidone cycloaddition butadiene.

The thiazolidonespirocyclohexenes I (R = MeO, R1 = Me, PhCH2; R = Ph, p-ClC6H4, R1 = PhCH2) were prepared by treating the thiazolone II with CH2:CMeCMe:CH2.

Chemical & Pharmaceutical Bulletin published new progress about Cycloaddition reaction. 10574-69-3 belongs to class thiazole, and the molecular formula is C10H9NOS2, Name: 3-Benzyl-2-thioxothiazolidin-4-one.

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

Chen, Lingfeng; Chen, Hongjin; Chen, Pengqin; Zhang, Wenxin; Wu, Chao; Sun, Chuchu; Luo, Wu; Zheng, Lulu; Liu, Zhiguo; Liang, Guang published the artcile< Development of 2-amino-4-phenylthiazole analogues to disrupt myeloid differentiation factor 88 and prevent inflammatory responses in acute lung injury>, Name: 2-Amino-4-(3-nitrophenyl)thiazole, the main research area is piperazinyl phenylthiazolylpropanamide preparation MyD88 protein homodimerization inhibitor antiinflammatory; 2-Amino-4-phenylthiazole; Acute lung injury; Anti-inflammation; Macrophages; MyD88.

The synthesis of 47 new analogs by modifying different sites on this lead compound and assessed their anti-inflammatory activities in lipopolysaccharide-induced mouse primary peritoneal macrophages (MPMs) was described. The most promising compound I was found to effectively interact with MyD88 protein and prevented formation of the MyD88 homodimeric complex. Furthermore, compound I showed in-vivo anti-inflammatory activity in LPS-caused model of acute lung injury. This work provided new candidates as MyD88 inhibitors to combat inflammation diseases.

European Journal of Medicinal Chemistry published new progress about Alkyl aryl ketones Role: RCT (Reactant), RACT (Reactant or Reagent). 57493-24-0 belongs to class thiazole, and the molecular formula is C9H7N3O2S, Name: 2-Amino-4-(3-nitrophenyl)thiazole.

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

Pulici, Maurizio; Quartieri, Francesca published the artcile< Traceless solid-phase synthesis of 2-amino-5-alkylidene-thiazol-4-ones>, Name: 3-Benzyl-2-thioxothiazolidin-4-one, the main research area is polymer supported rhodanine arylaldehyde Knoevenagel condensation amine resin cleavage; aminoalkyldiene thiazolone stereoselective preparation.

2-Amino-5-alkylidene-thiazol-4-ones, e.g., I, bearing two diversity points were prepared by a solid-phase strategy exploiting rhodanine as the starting material. Rhodanine was first loaded on bromo-Wang resin, subjected to Knoevenagel condensation with aldehydes, and cleaved off the resin in a traceless manner by means of an amine.

Tetrahedron Letters published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 10574-69-3 belongs to class thiazole, and the molecular formula is C10H9NOS2, Name: 3-Benzyl-2-thioxothiazolidin-4-one.

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