Category: iodides-buliding-blocks

Gronowitz, Salo; Vilks, Vija published the artcile< Iodo thiophenes and bithienyls>, Product Details of C6H5IO2S, the main research area is .

Iodo thiophenes could be prepared by the reaction of thiophene with iodine and HIO3 to give 2,3,5-triiodothiophene (I), from which other iodothiophenes were obtained. I, m. 82-5° (EtOH), was prepared in 77% yield by refluxing for 100 hrs. a mixture of 1.25 moles thiophene, 800 ml. HOAc, 369 ml. H2O,300 ml. CCl4, 21 ml. concentrated H2SO4, 1.5 moles iodine, and 0.77 moles HIO3, adding H2O and CCl4, extracting, washing, drying, and removing CCl4. A solution of 0.1 mole I in 300 ml. anhydrous Et2O was added to 100 ml. 1.03N BuLi at -70° to give a 63% yield of 2,4-diiodothiophene (II), b10 142-4.5°, which, when added then to an equivalent amount of BuLi at -70° and the resulting solution poured onto CO2 and hydrolyzed, gave 53% 4-iodo-2-thiophene-carboxylic acid (III), m. 115-17°; Me ester m. 41.5-3°. The reaction of 2 moles BuLi with 1 mole II gave 80% 2,4-thiophenedicarboxylic acid, m. 299-301°. Addition of 0.238 moles I continuously to a boiling mixture of 100 ml. H2O, 70 g. Zn powder, and 40 ml. HOAc with immediate distillation of the product gave 25.5 g. (52%) 3-iodothiophene (IV), b9 66-8°, n20D 1.6584, and 10 g. thiophene. The reaction of IV with iodine-HIO3 gave 73% 2,3-diiodothiophene (V), b10 133-5°, and 0.5% II, whereas the reaction of IV in C6H6 with HgO and iodine gave a mixture b14 14650°, which was shown by infrared analysis to contain 93% V and 7% II. Iodination of Me 2-thiophenecarboxylate with iodine and HIO3 gave 45% Me 5-iodo-2-thiophenecarboxylate (VI), m. 88-9° (ligroine), containing 3% Me 4-iodo-2-thiophenecarboxylate. Refluxing VI 10 hrs. with methanolic KOH gave 80% 5-iodo-2-thiophenecarboxylic acid, m. 132-4° (EtOH). To 33 g. 5,5′-dicarboxy-2,2′-bithienyl, prepared by refluxing BuLi and 2,2′-bithienyl and pouring the mixture onto CO2, was added dropwise 60 g. SOCl2, the mixture refluxed 60 hrs., excess SOCl2 removed, 150 ml. anhydrous MeOH added dropwise, and the mixture refluxed 21 hrs. to give 31 g. (85%) 5,5′-dicarbomethoxy-2,2′-bi-thienyl (VII), m. 208-10°. Addition of 26 g. iodine to a mixture of 28 g. VII and 32 g. Hg(OAc)2 in HOAc at 95° followed by stirring at 100° for 72 hrs. and continuously extracting with Et2O for 72 hrs. gave 26.6 g. (65%) 3-iodo-5,5′-dicarbomethoxy-2,2′-bithienyl, m. 127.5-9° (ligroine). To BuLi at -70° was added 2,3-di-iodothiophene in Et2O, then CuCl2, and the mixture worked up to give 25% 3,3′-diiodo-2,2′-bithienyl (VIII), m. 149.5-51° (ligroine). Prepared similarly from I was 3,3′,5,5′-tetraiodo-2,2′-bi-thienyl, m. 190.5-2° (ligroine).

Arkiv foer Kemi published new progress about IR spectra. 88105-22-0 belongs to class iodides-buliding-blocks, and the molecular formula is C6H5IO2S, Product Details of C6H5IO2S.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Ting, Chi P.; Tschanen, Esther; Jang, Esther; Maimone, Thomas J. published the artcile< Total synthesis of podophyllotoxin and select analog designs via C-H activation>, Name: Methyl 5-iodothiophene-2-carboxylate, the main research area is podophyllotoxin analog synthesis arylation.

An account of our previously disclosed total synthesis of the aryltetralin lignan natural product podophyllotoxin, a building block used in the synthesis of the FDA-approved anticancer drug etoposide, is disclosed. A C-H activation disconnection was viewed as being amenable to the preparation of E-ring modified analogs but proved challenging to execute. Various insights into palladium-catalyzed C-H arylation reactions on complex scaffolds are reported ultimately leading to the implementation of this strategy and the synthesis of compounds inaccessible by semisynthetic means.

Tetrahedron published new progress about Arylation. 88105-22-0 belongs to class iodides-buliding-blocks, and the molecular formula is C6H5IO2S, Name: Methyl 5-iodothiophene-2-carboxylate.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Lindstroem, Stefan; Ripa, Lena; Hallberg, Anders published the artcile< Synthesis of Two Conformationally Constrained Analogues of the Minor Tobacco Alkaloid Anabasine>, Quality Control of 188057-20-7, the main research area is anabasine spiro analog preparation.

The anabasine analogs spiro[4-azaindan-1,2′-piperidine] and spiro[6-azaindan-1,2′-piperidine] have been prepared A series of palladium-catalyzed reactions, where an intramol. cyclization constituted a key reaction, were utilized for the preparation of the two target compounds

Organic Letters published new progress about Cyclization. 188057-20-7 belongs to class iodides-buliding-blocks, and the molecular formula is C5H4INO, Quality Control of 188057-20-7.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Brea, Oriana; Szabo, Kalman J.; Himo, Fahmi published the artcile< Mechanisms of Formation and Rearrangement of Benziodoxole-Based CF3 and SCF3 Transfer Reagents>, SDS of cas: 1391728-13-4, the main research area is benziodoxole based trifluoromethyl trifluoromethylthio group transfer reagent formation rearrangement.

Togni’s benziodoxole-based reagents are widely used in trifluoromethylation reactions. It has been established that the kinetically stable hypervalent iodine form (I-CF3) of the reagents is thermodynamically less stable than its acyclic ether isomer (O-CF3). On the other hand, the trifluoromethylthio analog exists in the thermodynamically stable thioperoxide form (O-SCF3), and the hypervalent form (I-SCF3) has been elusive. Despite the importance of these reagents, very little is known about the reaction mechanisms of their syntheses, which has hampered the development of new reagents of the same family. Herein, we use d. functional theory calculations to understand the reasons for the divergent behaviors between the CF3 and SCF3 reagents. We demonstrate that they follow different mechanisms of formation and that the metals involved in the syntheses (potassium in the case of the trifluoromethyl reagent and silver in the trifluoromethylthio analog) play key roles in the mechanisms and greatly influence the possibility of their rearrangements from the hypervalent (I-CF3, I-SCF3) to the corresponding ether-type form (O-CF3, O-SCF3).

Journal of Organic Chemistry published new progress about Free energy of activation. 1391728-13-4 belongs to class iodides-buliding-blocks, and the molecular formula is C9H10FIO, SDS of cas: 1391728-13-4.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Klimankova, Iveta; Hubalek, Martin; Matousek, Vaclav; Beier, Petr published the artcile< Synthesis of water-soluble hypervalent iodine reagents for fluoroalkylation of biological thiols>, Application In Synthesis of 1391728-13-4, the main research area is fluoroalkyl iodonium benzoiodoxole preparation water soluble fluoroalkylation reagent; stability chemoselectivity fluoroalkylation thiol cysteine fluoroalkyl iodonium benzoiodoxole.

Water-soluble fluoroalkyl iodonium compounds and fluoroalkyl benzoiodanes were prepared and tested for their ability to alkylate the sulfur atoms of cysteine and cysteine-containing peptides under biocompatible conditions. Some of the reagents displayed excellent reactivity despite their limited stability in aqueous media. In reactions with a cysteine-containing heptapeptide, in addition to the expected S-fluoroalkylated product, a range of side-products were obtained, with the amounts of side-products depending on the conditions used (type of reagent, concentration, and pH). With highly activated hypervalent iodine reagents, a new reactive mode was observed – reaction with disulfides to form fluoroalkyl thiols.

Organic & Biomolecular Chemistry published new progress about Disulfides Role: RCT (Reactant), RACT (Reactant or Reagent). 1391728-13-4 belongs to class iodides-buliding-blocks, and the molecular formula is C9H10FIO, Application In Synthesis of 1391728-13-4.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Bag, Subhendu Sekhar; Talukdar, Sangita; Anjali, S. J. published the artcile< Regioselective and stereoselective route to N2-β-tetrazolyl unnatural nucleosides via SN2 reaction at the anomeric center of Hoffer's chloro-sugar>, Related Products of 887266-99-1, the main research area is transition state nucleophilic substitution nucleoside tetrazole preparation crystal structure; regioselective stereoselective substitution DNA nucleoside tetrazole steric effect DFT; 2,5-Disubstituted tetrazoles; Regioselective; S(N)2 reaction; Stereoselective; Tetrazolyl-N2-β-nucleosides.

We are reporting a regioselective and stereoselective route to N2-β-tetrazolyl aromatic donor/acceptor unnatural nucleosides as new class of possible DNA base analogs. The SN2 substitution reaction at the anomeric center of Hoffer’s chloro-sugar with various 5-substituted aromatic tetrazoles in THF in presence of K2CO3 proceeds with regioselectivity at N2-tetrazoles and stereoselectivity at α-chloro-sugar with very good yield. The stereoelectronic and steric effects play a crucial role for the observed outcome which is also supported from a theor. DFT study. The methodol. is simple, eco-compatible and the tetrazolyl unnatural nucleosides might find applications in decorating DNA for various biotechnol. and DNA based material science applications.

Bioorganic & Medicinal Chemistry Letters published new progress about Crystal structure. 887266-99-1 belongs to class iodides-buliding-blocks, and the molecular formula is C7H3FIN, Related Products of 887266-99-1.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

D’Auria, Maurizio; Mauriello, Giacomo published the artcile< Bis(trifluoroacetoxy)iodobenzene-iodine system: an efficient and selective reagent for iodination of thiophene derivatives>, Application In Synthesis of 88105-22-0, the main research area is iodination thiophene trifluoroacetoxyiodobenzene iodide.

Bis-(trifluoroacetoxy)iodobenzene-iodine system is a good iodinating reagent of thiophene derivatives giving products with iodine atom in α-position on the thiophene ring. For example, iodination of 2-thiophenecarboxylic acid Me ester with bis(trifluoroacetoxy)iodobenzene/iodine gave 5-iodo-2-thiophenecarboxylic acid Me ester in 78% yield.

Tetrahedron Letters published new progress about Iodination, regioselective. 88105-22-0 belongs to class iodides-buliding-blocks, and the molecular formula is C6H5IO2S, Application In Synthesis of 88105-22-0.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Muthukaman, Nagarajan; Deshmukh, Sanjay; Tondlekar, Shital; Tambe, Macchindra; Pisal, Dnyandeo; Sarode, Neelam; Mhatre, Siddharth; Chakraborti, Samitabh; Shah, Daisy; Bhosale, Vikram M.; Kulkarni, Abhay; Mahat, Mahamad Yunnus A.; Jadhav, Satyawan B.; Gudi, Girish S.; Khairatkar-Joshi, Neelima; Gharat, Laxmikant A. published the artcile< Discovery of 5-(2-chloro-4'-(1H-imidazol-1-yl)-[1,1'-biphenyl]-4-yl)-1H-tetrazole as potent and orally efficacious S-nitrosoglutathione reductase (GSNOR) inhibitors for the potential treatment of COPD>, HPLC of Formula: 887266-99-1, the main research area is imidazolyl biaryl carboxylic acid preparation nitrosoglutathione reductase inhibition SAR; biaryl imidazolyl tetrazole preparation nitrosoglutathione reductase inhibition SAR; Bioavailability; Bronchodilation; Cigarette smoke (CS); GSNOR inhibitor; Glutathione (GSH); Reductase; S-nitrosoglutathione (GSNO).

Design, synthesis and structure-activity relationships (SAR) of novel imidazole-biaryl-tetrazole I [X = C, N; R1 = H, Me, F, Cl, CF3; R2 = H, Me, Et, Cl, cyclopropyl; R3 = H, Me] based GSNOR inhibitors were described. Many potent inhibitor compounds I [X = C, R1 = Cl, R2 = R3 = H; X = C, R1 = R3 = H, R2 = Me, Et; X = C, R1 = Cl, R2 = Me, R3 = H; X = C, R1 = F, R2 = Et, R3 = H; X = N, R1 = F, R2 = Me, R3 = H] and II [X = C, R1 = H, R2 = Me] were identified with low nanomolar activity (IC50s: <15 nM) along with adequate metabolic stability. Lead compounds I [X = C, R1 = Cl, R2 = R3 = H; X = N, R1 = F, R2 = Me, R3 = H] exhibited good exposure and oral bioavailability in mouse pharmacokinetic (PK) study. Compound I [X = C, R1 = Cl, R2 = R3 = H] was selected for further profiling and revealed comparable mouse and rat GSNOR potency, high selectivity against alc. dehydrogenase (ADH) and carbonyl reductase (CBR1) family of enzymes, low efflux ratio and permeability in PAMPA, a high permeability in CALU-3 assay, significantly low hERG activity and minimal off-target activity. Further, an in-vivo efficacy of compound I [X = C, R1 = Cl, R2 = R3 = H] was disclosed in cigarette smoke (CS) induced mouse model for COPD. Bioorganic & Medicinal Chemistry Letters published new progress about Alcohol dehydrogenase inhibitors. 887266-99-1 belongs to class iodides-buliding-blocks, and the molecular formula is C7H3FIN, HPLC of Formula: 887266-99-1.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

D’Auria, Maurizio; De Mico, Antonella; D’Onofrio, Franco; Mendola, Daniele; Piancatelli, Giovanni published the artcile< Photochemical behavior of halothiophenes: synthesis of 5-arylthiophene-2-carboxylic esters>, Name: Methyl 5-iodothiophene-2-carboxylate, the main research area is photolysis halothiophene derivative reactivity mechanism; bithiophenecarboxylic acid propynyl; arylation photochem halothiophene derivative.

The arylation of 5-halothiophene-2-carbonitrile and Me 5-halothiophene-2-carboxylate by a photochem. process was investigated. Whereas 5-bromothiophene-2-carbonitrile is completely unreactive, the corresponding iodo derivative furnishes the dehalogenation product. In contrast, Me 5-iodothiophene-2-carboxylate gives the corresponding aryl and heteroaryl derivatives in good yields on irradiation in the presence of various aromatic substrates (benzene, p-xylene, naphthalene, thiophene, 2-bromothiophene and 2-chlorothiophene). The different reactivities of these compounds are explained. An application of this conversion to the synthesis of 5′-(1-propynyl)-2,2′-bithiophene-5-carboxylic acid is reported.

Journal of Photochemistry and Photobiology, A: Chemistry published new progress about Phosphorescence. 88105-22-0 belongs to class iodides-buliding-blocks, and the molecular formula is C6H5IO2S, Name: Methyl 5-iodothiophene-2-carboxylate.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Yang, Peng-Fei; Shu, Wei published the artcile< Orthogonal Access to α-/β-Branched/Linear Aliphatic Amines by Catalyst-Tuned Regiodivergent Hydroalkylations>, Name: tert-Butyl (3-iodopropyl)carbamate, the main research area is amine preparation regioselective; chiral amine preparation regioselective enantioselective; alkenyl amine alkyl halide hydroalkylation metal catalyst; Amines; Chain Walking; Cobalt Catalysis; Hydroalkylations; Regiodivergent Reactions.

Herein, a catalyst-controlled synthesis of α-branched e.g., N-(1-phenylpentan-3-yl)benzamide, β-branched e.g., N-(2-methyl-4-phenylbutyl)benzamide and linear aliphatic amines e.g., N-(5-phenylpentyl)benzamide from Ni/Co-catalyzed regio- and site-selective hydroalkylations of alkenyl amines e.g., N-(prop-2-en-1-yl)benzamide with alkyl halides RX (R = butan-2-yl, Bn, 2-phenylethyl, 2-(1,3-dioxolan-2-yl)ethyl, etc.; X = I, Br) is developed. This catalytic protocol features the reliable prediction and control of the coupling position of alkylation to provide orthogonal access to α-branched, β-branched and linear alkyl amines from identical starting materials. This platform unlocks orthogonal reactivity and selectivity of nickel hydride and cobalt hydride chem. to catalytically repurpose three types of alkyl amines under mild conditions.

Angewandte Chemie, International Edition published new progress about Aliphatic amines Role: SPN (Synthetic Preparation), PREP (Preparation). 167479-01-8 belongs to class iodides-buliding-blocks, and the molecular formula is C8H16INO2, Name: tert-Butyl (3-iodopropyl)carbamate.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com