23152-99-0Relevant academic research and scientific papers
Piers′ Borane-Induced Tetramerization of Arylacetylenes
Hasenbeck, Max,Müller, Tizian,Averdunk, Arthur,Becker, Jonathan,Gellrich, Urs
supporting information, (2022/01/04)
We herein report that the reaction of Piers′ borane, i. e. HB(C6F5)2, with an excess of arylacetylenes at room temperature leads to tetramerization of the acetylene and the diastereoselective formation of boryl-substituted
DBU-Mediated Synthesis of Aryl Acetylenes or 1-Bromoethynylarenes from Aldehydes
Thummala, Yadagiri,Karunakar, Galla V.,Doddi, Venkata Ramana
supporting information, p. 611 - 616 (2019/01/04)
Two well known synthetic organic reactions Ramirez olefination and Corey-fuchs reactions are integrated in one-pot sequential manner for the synthesis of arylacetylenes and 1,3-enynes starting directly from commercially available aldehydes. The bicyclic amidine 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) along with additive NaOH not only exclusively afforded the terminal alkynes directly from the aldehydes, but also enhanced the reaction rate. The dynamic nature of DBU also facilitated the isolation of 1-bromoalkynes intermediate products. Selection of additive from NaOH and H2O served as a switch for the synthesis of terminal alkyne and 1-bromoalkynes, respectively. (Figure presented.).
Calcium carbide catalytically activated with tetra-: N -butyl ammonium fluoride for Sonogashira cross coupling reactions
Hosseini, Abolfazl,Pilevar, Afsaneh,Hogan, Eimear,Mogwitz, Boris,Schulze, Anne S.,Schreiner, Peter R.
, p. 6800 - 6807 (2017/08/22)
We report a novel method for the direct synthesis of mono- and bis-arylated alkynes utilizing catalytically activated CaC2 as the alkyne component. This fluoride-activated cross coupling reaction provides advantages over existing methods regarding operational simplicity, use of readily available starting materials, and low cost.
Catalytic cascade hydroalkoxylation/isomerization/[4 + 2] cycloaddition using enyne alcohols as latent dienes or dienophiles
Guo, Rui,Li, Kang-Nan,Gong, Liu-Zhu
supporting information, p. 6707 - 6712 (2013/10/01)
Enyne alcohols can react as precursors of either dienes or dienophiles with different substrates after hydroxylation and isomerization by gold catalysis. As such, oxa-bridged tricyclo[5.2.2.02,6]undec-8-ene-3,5-dione derivatives have been obtained by the Diels-Alder reaction and tetrahydro-1H-furo[3,4-c]pyran derivatives could be accessed by the hetero-Diels-Alder cycloaddition.
One-pot, two-step conversion of aldehydes to phosphonyl- and sulfonylpyrazoles using Bestmann-Ohira reagent
Kumar, Rahul,Verma, Deepti,Mobin, Shaikh M.,Namboothiri, Irishi N. N.
supporting information; experimental part, p. 4070 - 4073 (2012/09/21)
A one-pot, two-step, three-component method for the conversion of commercially available aldehydes to phosphonylpyrazoles has been developed, demonstrating, for the first time, the dual reactivity of the Bestmann-Ohira reagent (BOR) in a single-pot transformation. This method, extended to the synthesis of sulfonylpyrazoles by employing BOR in the first step and a diazomethyl sulfone in the second step, is complementary, with regard to regioselectivity, to the previous methods for the synthesis of such functionalized pyrazoles.
Convenient synthesis of terminal alkynes from anti-3-aryl-2,3- dibromopropanoic acids using a K2CO3/DMSO system
Cheng, Xuezhi,Jia, Jun,Kuang, Chunxiang
, p. 2350 - 2354 (2012/02/03)
A convenient, efficient, and generally applicable method was developed for the synthesis of terminal alkynes from anti-3-aryl-2,3-dibromopropanoic acids in the presence of DMSO and K2CO3.
4-Amino-5-aryl-6-arylethynylpyrimidines: Structure-activity relationships of non-nucleoside adenosine kinase inhibitors
Matulenko, Mark A.,Paight, Ernest S.,Frey, Robin R.,Gomtsyan, Arthur,DiDomenico Jr., Stanley,Jiang, Meiqun,Lee, Chih-Hung,Stewart, Andrew O.,Yu, Haixia,Kohlhaas, Kathy L.,Alexander, Karen M.,McGaraughty, Steve,Mikusa, Joseph,Marsh, Kennan C.,Muchmore, Steven W.,Jakob, Clarissa L.,Kowaluk, Elizabeth A.,Jarvis, Michael F.,Bhagwat, Shripad S.
, p. 1586 - 1605 (2008/02/01)
A series of non-nucleoside adenosine kinase (AK) inhibitors is reported. These inhibitors originated from the modification of 5-(3-bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-ylamine (ABT-702). The identification of a linker that would approximate the spatial arrangement found between the pyrimidine ring and the aryl group at C(7) in ABT-702 was a key element in this modification. A search of potential linkers led to the discovery of an acetylene moiety as a suitable scaffold. It was hypothesized that the aryl acetylenes, ABT-702, and adenosine bound to the active site of AK (closed form) in a similar manner with respect to the orientation of the heterocyclic base. Although potent acetylene analogs were discovered based on this assumption, an X-ray crystal structure of 5-(4-dimethylaminophenyl)-6-(6-morpholin-4-ylpyridin-3-ylethynyl)pyrimidin-4-ylamine (16a) revealed a binding orientation contrary to adenosine. In addition, this compound bound tightly to a unique open conformation of AK. The structure-activity relationships and unique ligand orientation and protein conformation are discussed.
5,6,7-Trisubstituted 4-Aminopyrido[2,3-d]pyrimidines as Novel Inhibitors of Adenosine Kinase
Perner, Richard J.,Gu, Yu-Gui,Lee, Chih-Hung,Bayburt, Erol K.,McKie, Jeffery,Alexander, Karen M.,Kohlhaas, Kathy L.,Wismer, Carol T.,Mikusa, Joe,Jarvis, Michael F.,Kowaluk, Elizabeth A.,Bhagwat, Shripad S.
, p. 5249 - 5257 (2007/10/03)
The synthesis and structure-activity relationship of a series of 5,6,7-trisubstituted 4-aminopyrido[2,3-d]pyrimidines as novel nonnucleoside adenosine kinase inhibitors is described. A variety of alkyl, aryl, and heteroaryl substituents were found to be tolerated at the C5, C6, and C7 positions of the pyridopyrimidine core. These studies have led to the identification of analogues that are potent inhibitors of adenosine kinase with in vivo analgesic activity.
5,6,7-trisubstituted-4-aminopyrido[2,3-D] pyrimidine compounds
-
, (2008/06/13)
A compound having the formula wherein R1, R2, R3, R4 and R5 are defined, a method for inhibiting adenosine kinase by administering a compound thereof, a pharmaceutical composition comprising a therapeutically effective amount of a compound thereof above i
Synthesis and antimicrobial activity of new 2-phenylethynylbenzothiazoles and related salts
Magdolen,Zahradnik,Foltinova
, p. 1023 - 1027 (2007/10/03)
New 2-phenylethynylbenzothiazoles were synthesized by coupling reaction between 2-iodobenzothiazole and substituted phenylacetylenes under palladium catalysis. The modified Wittig reaction was used to prepare the substituted phenylacetylenes from correspo
