7223-30-5Relevant academic research and scientific papers
Ring Opening/Site Selective Cleavage in N-Acyl Glutarimide to Synthesize Primary Amides
Govindan, Karthick,Lin, Wei-Yu
supporting information, p. 1600 - 1605 (2021/03/03)
A LiOH-promoted hydrolysis selective C-N cleavage of twisted N-acyl glutarimide for the synthesis of primary amides under mild conditions has been developed. The reaction is triggered by a ring opening of glutarimide followed by C-N cleavage to afford primary amides using 2 equiv of LiOH as the base at room temperature. The efficacy of the reactions was considered and administrated for various aryl and alkyl substituents in good yield with high selectivity. Moreover, gram-scale synthesis of primary amides using a continuous flow method was achieved. It is noted that our new methodology can apply under both batch and flow conditions for synthetic and industrial applications.
Z-Selective phosphine promoted 1,4-reduction of ynoates and propynoic amides in the presence of water
Drikermann, Denis,Kupfer, Stephan,Seifert, Fabian,Steinmetzer, Johannes,Vilotijevic, Ivan,Zi, You
, p. 6092 - 6097 (2021/07/21)
Phosphine-mediated reductions of substituted propynoic esters and amides in the presence of water yield the partially reduced α,β-unsaturated esters and amides with highZ-selectivity. The competitivein situ ZtoE-isomerization of the product in some cases lowers theZtoEratios of the isolated α,β-unsaturated carbonyl products. Reaction time and the amounts of phosphine and water in the reaction mixture are the key experimental factors which control the selectivity by preventing or reducing the rates ofZ- toE-product isomerization. Close reaction monitoring enables isolation of theZ-alkenes with high selectivities. The computational results suggest that the reactions could be highlyZ-selective owing to the stereoselective formation of theE-P-hydroxyphosphorane intermediate.
AlBr3-Promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes: Synthesis of 3,3-diarylpropenenitriles
Gorbunova, Yelizaveta,Ryabukhin, Dmitry S.,Vasilyev, Aleksander V.
, p. 2663 - 2667 (2021/11/30)
Reactions of 3-arylpropynenitriles (ArC≡CCN) with electron-rich arenes (Ar'H, benzene and its polymethylated derivatives) under the action of aluminum bromide (AlBr3, 6 equiv) at room temperature for 0.5-2 h result in the stereoselective formation of 3,3-
N-triflyl-propiolamides: Preparation and transamidation reactions
Fiore, Vito A.,Maas, Gerhard
, p. 3586 - 3595 (2019/05/27)
N-Trifluoromethylsulfonyl-propiolamides have been prepared by two methods: a) N-triflation of secondary acetylenic carboxanilides, prepared in two steps from terminal alkynes, with triflic anhydride (Tf2O) and b) from terminal alkynes and an aryl or alkyl isocyanate followed by Tf2O in a consecutive one-pot reaction. The title compounds are bench-stable and insensitive to water and alcohols but amenable to transamidation reactions with a wide range of amine nucleophiles. Conversely, they are excellent reagents for the propynoylation of ammonia, primary and secondary amines, anilines, and hydrazines.
Water as a Hydrogenating Agent: Stereodivergent Pd-Catalyzed Semihydrogenation of Alkynes
Zhao, Chuan-Qi,Chen, Yue-Gang,Qiu, Hui,Wei, Lei,Fang, Ping,Mei, Tian-Sheng
supporting information, p. 1412 - 1416 (2019/03/07)
Palladium-catalyzed transfer semihydrogenation of alkynes using H2O as the hydrogen source and Mn as the reducing reagent is developed, affording cis- and trans-alkenes selectively under mild conditions. In addition, this method provides an efficient way to access various cis-1,2-dideuterioalkenes and trans-1,2-dideuterioalkenes by using D2O instead of H2O.
One-pot tandem hydrophenylation and ionic hydrogenation of 3-phenylpropynoic acid derivatives under superelectrophilic activation
Nilov, Denis I.,Vasilyev, Aleksander V.
supporting information, p. 5714 - 5717 (2015/09/29)
The reactions of esters and amides of 3-phenylpropynoic acid with strong Lewis acids AlX3 (X = Cl, Br) or conjugate Br?nsted-Lewis superacids HX-AlX3 (X = Cl, Br) in benzene and cyclohexane at room temperature afforded 3,3-diphenylpropanoic acid derivatives in up to 94% yield. This tandem reaction of the acetylene bond proceeded by hydrophenylation followed by ionic hydrogenation.
Optimization and Evaluation of 5-Styryl-Oxathiazol-2-one Mycobacterium tuberculosis Proteasome Inhibitors as Potential Antitubercular Agents
Russo, Francesco,Gising, Johan,?kerbladh, Linda,Roos, Annette K.,Naworyta, Agata,Mowbray, Sherry L.,Sokolowski, Anders,Henderson, Ian,Alling, Torey,Bailey, Mai A.,Files, Megan,Parish, Tanya,Karlén, Anders,Larhed, Mats
, p. 342 - 362 (2015/06/30)
This is the first report of 5-styryl-oxathiazol-2-ones as inhibitors of the Mycobacterium tuberculosis (Mtb) proteasome. As part of the study, the structure-activity relationship of oxathiazolones as Mtb proteasome inhibitors has been investigated. Furthermore, the prepared compounds displayed a good selectivity profile for Mtb compared to the human proteasome. The 5-styryl-oxathiazol-2-one inhibitors identified showed little activity against replicating Mtb, but were rapidly bactericidal against nonreplicating bacteria. (E)-5-(4-Chlorostyryl)-1,3,4-oxathiazol-2-one) was most effective, reducing the colony-forming units (CFU)/mL below the detection limit in only seven days at all concentrations tested. The results suggest that this new class of Mtb proteasome inhibitors has the potential to be further developed into novel antitubercular agents for synergistic combination therapies with existing drugs.
A general and practical oxidation of alcohols to primary amides under metal-free conditions
Wu, Xiao-Feng,Sharif, Muhammad,Feng, Jian-Bo,Neumann, Helfried,Pews-Davtyan, Anahit,Langer, Peter,Beller, Matthias
, p. 1956 - 1961 (2013/09/24)
A general procedure for oxidation of both benzyl alcohols and alkyl alcohols to primary amides under catalyst free conditions has been developed. 34 examples of primary amides were produced from their corresponding alcohols in moderate to excellent yields. This is a practical procedure for primary amides synthesis; water and tert-butanol are the only by-products. A commercial drug, Piracetam, was prepared in one step with 73% yield as well.
Preparation of primary amides from functionalized organozinc halides
Schade, Matthias A.,Manolikakes, Georg,Knochel, Paul
supporting information; experimental part, p. 3648 - 3650 (2010/11/04)
Organozinc halides, which are prepared either by direct zinc insertion or halogen-magnesium exchange and subsequent transmetalation with ZnCl2, react smoothly with commercially available trichloroacetyl isocyanate to give, after hydrolysis, the corresponding primary amides. This method is compatible with a variety of functional groups such as an ester or a cyano group. Also heterocyclic-, alkenyl, and acetylenic zinc reagents are converted to the corresponding primary amides under these conditions.
Novel and direct transformation of methyl ketones or carbinols to primary amides by employing aqueous ammonia
Cao, Liping,Ding, Jiaoyang,Gao, Meng,Wang, Zihua,Li, Juan,Wu, Anxin
supporting information; experimental part, p. 3810 - 3813 (2009/12/06)
Figur Presented A novel and direct transformation of aryl, heteroaryl, vinyl, or ethynyl methyl ketones or carbinols to corresponding primary amides has been developed. An iodine-NH3·H2O system was proven to be efficient for this reaction and afforded the expected products with good yields in aqueous media. A tandem Lieben-Haller-Bauer reaction mechanism was involved in this type of reaction and is proposed for the first time.
