127-66-2Relevant articles and documents
Synthesis of alkyne derivatives of a novel triazolopyrazine as A 2A adenosine receptor antagonists
Yao, Gang,Haque, Serajul,Sha, Li,Kumaravel, Gnanasambandam,Wang, Joy,Engber, Thomas M.,Whalley, Eric T.,Conlon, Patrick R.,Chang, Hexi,Kiesman, William F.,Petter, Russell C.
, p. 511 - 515 (2005)
A novel [1,2,4]triazolo[1,5-a]pyrazine core was synthesized and coupled with terminal acetylenes. The structure-activity relationship of the alkynes from this novel template was studied for their in vitro and in vivo adenosine A2A receptor antagonism. Selected compounds from this series were shown to have potent in vitro and in vivo activities against adenosine A 2A receptor. Compound 12, in particular, was found to be orally active at 3 mg/kg in both a mouse catalepsy model and a 6-hydroxydopamine- lesioned rat model.
Further chemistry of ruthenium alkenyl acetylide complexes: Routes to allenylidene complexes via a series of electrophilic addition reactions
Hall, Michael R.,Korb, Marcus,Moggach, Stephen A.,Low, Paul J.
, p. 2838 - 2853 (2020/10/02)
The methyl substituents in the cationic allenylidene complexes trans-[Ru{C=C=C(Me)R}Cl(dppe)2]OTf ([1a?f]OTf) are readily deprotonated to give the corresponding alkenyl acetylide complexes trans-[Ru{C=CC(=CH2)R}Cl(dppe)2] (3; R = Me (a), Ph (b), cC5H10 (c), 4-MeS-C6H4 (d), cC4H3S (e), cC5H4N (f)). Similar chemistry is also observed from [Ru{C=C=C(Me)Ph}(dppe)Cp*]PF6 ([2b]PF6) and [Ru{C=C=C(Me)(4-MeS-C6H4)}(dppe)Cp*]PF6([2b]PF6), chosen to broaden the reaction scope, giving [Ru{C= CC(=CH2)Ph}(dppe)Cp*] (4b) and [Ru{C=C=C(CH2)(4-MeS-C6H4)}(dppe)Cp*] (4d). In turn, reactions of 3b,d and 4b,d with the [BF4]? salt of the electrophilic tritylium [CPh3]+ cation give the functionalized allenylidene complexes trans-[Ru{C=C=C(CH2CPh3)R}Cl(dppe)2]BF4 ([5b,d]BF4) and [Ru{C=C=C(CH2CPh3)R}(dppe)Cp*]BF4 ([6b,d]BF4) formed by addition of the electrophile to the remote vinylic carbon (C(δ)). Although trans-[Ru{C=C=C(CH2CPh3)Me}Cl(dppe)2]BF4 ([5a]BF4) could not be successfully purified from reactions of 3a with [CPh3]BF4, deprotonation of the crude product gave the Zaitsev vinyl product trans-[Ru{C=CC(=CHCPh3)Me}Cl(dppe)2] (7a) in good yield. The initial cycloheptatrienyl adducts formed from reactions of 3b,d and 4b,d with the tropylium salt [C7H7]BF4 undergo a ring-contraction process in chloroform solutions upon exposure to air, to give the styrene-like products trans-[Ru{C=C=C(R)C(H)=CHPh}Cl(dppe)2]BF4 ([10b,d]BF4) and [Ru{C=C= C(R)C(H)=CHPh}(dppe)Cp*]BF4 ([11b,d]BF4), through what is believed to be a radical mechanism mediated by triplet oxygen.
BTK Inhibitors and uses thereof
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, (2020/05/02)
The invention discloses a bruton's tyrosine kinase (BTK) inhibitor and use thereof. Specifically, the invention provides heteroaromatic compounds or stereoisomers, geometrical isomers, tautomers, racemates, nitrogen oxides, hydrates, solvates, metabolites and pharmaceutically acceptable salts or prodrugs thereof, and pharmaceutical compositions containing the heteroaromatic compounds; the invention also discloses use of the heteroaromatic compounds or the pharmaceutical compositions containing the heteroaromatic compounds in preparation of medicines; the medicines can be used for treating autoimmune diseases, inflammatory diseases or proliferative diseases.
Cycloisomerization of Conjugated Allenones into Furans under Mild Conditions Catalyzed by Ligandless Au Nanoparticles
Zorba, Leandros,Kidonakis, Marios,Saridakis, Iakovos,Stratakis, Manolis
supporting information, p. 5552 - 5555 (2019/08/01)
Au nanoparticles supported on TiO2 (1 mol %) catalyze the quantitative cycloisomerization of conjugated allenones into furans under very mild conditions. The reaction rate is accelerated by adding acetic acid (1 equiv), but the acid does not participate in the protodeauration step as in the corresponding Au(III)-catalyzed transformation. The process is purely heterogeneous, allowing thus the recycling and reuse of the catalyst effectively in several runs.
Kinetic Resolution of Tertiary Propargylic Alcohols by Enantioselective Cu?H-Catalyzed Si?O Coupling
Seliger, Jan,Dong, Xichang,Oestreich, Martin
supporting information, p. 1970 - 1974 (2019/01/29)
A broad range of tertiary propargylic alcohols were kinetically resolved by catalyst-controlled enantioselective silylation. This non-enzymatic kinetic resolution is catalyzed by a Cu?H species and makes use of the commercially available precatalyst MesCu/(R,R)-Ph-BPE and a simple hydrosilane as the resolving reagent. Both alkyl,aryl- as well as dialkyl-substituted propargylic alcohols participate, and especially high selectivity factors are achieved when the alkyne terminus carries a TIPS group, which also enables facile post-functionalization in this position (s up to 207).
Neighboring Carbonyl Group Assisted Oxyacetoxylation of Propargylic Carboxylates with Retention of Chirality under Metal Free Condition
Pradhan, Tapas R.,Mohapatra, Debendra K.
, p. 3605 - 3611 (2019/07/04)
A metal-free oxyacetoxylation method of primary, secondary and tertiary propargylic carboxylates with retention of chirality was presented. The reaction proceeds through the intramolecular nucleophilic attack of the neighboring carbonyl group on an alkynyliodonium intermediate. The process is general with broad substrate scope and is amenable for application to a variety of propargyl carboxylates including those obtained from natural products. Insight into the mechanistic pathway by isotopic labelling (using H2O18 and D2O) and controlled experiments confirmed. (Figure presented.).
Heterogeneous Acid-Catalyzed Racemization of Tertiary Alcohols
G?rbe, Tamás,Lihammar, Richard,B?ckvall, Jan -E.
, p. 77 - 80 (2017/12/07)
Tertiary alcohols are important structural motifs in natural products and building blocks in organic synthesis but only few methods are known for their enantioselective preparation. Chiral resolution is one of these approaches that leaves one enantiomer (50 % of the material) unaffected. An attractive method to increase the efficiency of those resolutions is to racemize the unaffected enantiomer. In the present work, we have developed a practical racemization protocol for tertiary alcohols. Five different acidic resin materials were tested. The Dowex 50WX8 was the resin of choice since it was capable of racemizing tertiary alcohols without any byproduct formation. Suitable solvents and a biphasic system were investigated, and the optimized system was capable of racemizing differently substituted tertiary alcohols.
Base-Catalyzed Borylation/B-O Elimination of Propynols and B2pin2 Delivering Tetrasubstituted Alkenylboronates
Kuang, Zhijie,Chen, Haohua,Yan, Jianxiang,Yang, Kai,Lan, Yu,Song, Qiuling
supporting information, p. 5153 - 5157 (2018/09/12)
An efficient approach to tetrasubstituted alkenylboronates via a cascade borylation/B-O elimination of propynols and B2pin2 was disclosed. A series of tetrasubstituted alkenylboronates were readily furnished with this strategy in good yields, with further transformations leading to tetrasubstituted alkenes and β-diketones demonstrating the synthetic potential of the alkenylboronates constructed by this strategy as versatile intermediates in organic synthesis.
Method for efficiently preparing alkynol
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Paragraph 0036; 0037; 0038; 0043; 0044; 0045; 0046, (2018/12/14)
The invention relates to a method for efficiently preparing alkynol, belongs to the field of preparation of chemical intermediates and chemicals, and particularly relates to a preparation method of alkynol. The preparation method comprises the following steps that 1, alkali metal is added into an anhydrous alcohols solvent; an alcohol-alkali metal solution is prepared; 2, a compound I is added into the alcohol-alkali metal solution; uniform stirring is performed; cooling is performed to be 0 DEG C or below; 3, acetylene is introduced through being metered at normal pressure; alkynol is obtained; 4, the alkynol solution after reaction is neutralized by ammonium chloride and a same alcohol mixed suspension system; 5, the neutralized mixed suspension system is filtered; after alcohols are recovered from filter liquid, reduced pressure distillation is performed to obtain an alkynol product. The method overcomes the defect that under the existing harsh reaction conditions of high pressure,liquid ammonia and the like, the solid potassium hydroxide feeding difficulty is avoided; under the ordinary pressure condition, the ketone compounds are converted into alkynol at high conversion rate. The method has the advantages of high conversion rate, simple process and good product purity.
Direct Substitution of Secondary and Tertiary Alcohols to Generate Sulfones under Catalyst- and Additive-Free Conditions
Liu, Yanan,Xie, Peizhong,Sun, Zuolian,Wo, Xiangyang,Gao, Cuiqing,Fu, Weishan,Loh, Teck-Peng
supporting information, p. 5353 - 5356 (2018/09/13)
An environmentally benign protocol that affords propargylic sulfones containing highly congested carbon centers from easily accessible alcohols and sulfinic acids with water as the only byproduct is reported. The reaction proceeded via an in situ dehydrative cross-coupling process by taking advantage of the synergetic actions of multiple hydrogen bonds rather than relying on an external catalyst and/or additives to achieve high product distribution.
