23351-08-8Relevant academic research and scientific papers
Pseudo-5-Fold-Symmetrical Ligand Drives Geometric Frustration in Porous Metal-Organic and Hydrogen-Bonded Frameworks
Haase, Frederik,Craig, Gavin A.,Bonneau, Micka?le,Sugimoto, Kunihisa,Furukawa, Shuhei
, p. 13839 - 13845 (2020)
Reticular framework materials thrive on designability, but unexpected reaction outcomes are crucial in exploring new structures and functionalities. By combining "incompatible"building blocks, we employed geometric frustration in reticular materials leadi
Utilization of caffeine carbon supported cobalt catalyst in the tandem synthesis of pyrroles from nitroarenes and alkenyl diols
Balasubramaniam, Bhuvaneshwari,Dhara, Partha,Gupta, Raju K.,Kundu, Sabuj,Panja, Dibyajyoti,Sau, Anirban
, p. 244 - 254 (2021/09/07)
Employing bio-waste caffeine carbon-supported heterogeneous cobalt catalyst, synthesis of various substituted pyrrole derivatives is reported. In this methodology, pyrroles were synthesized through coupling between nitroarenes and alkenyl diols in a tandem manner. Among all the heterogeneous catalysts Co(OAc)2-CC-800 displayed the highest catalytic activity. Preparative scale synthesis of pyrroles and synthesis of anti-tubercular agent 5-(4-(1H-pyrrol-1-yl)phenyl)-1,3,4-oxadiazole-2-thiol revealed the practical applicability of this protocol. Several kinetic experiments and Hammett studies were conducted to understand the probable mechanism and electronic effects on this transformation.
Ligand and Cu freeN-arylation of indoles, pyrroles and benzylamines with aryl halides catalyzed by a Pd nanocatalyst
Paul, Abhijit,Chatterjee, Debnath,Banerjee, Srirupa,Yadav, Somnath
supporting information, p. 14447 - 14452 (2020/09/21)
Herein, theN-arylation of aromatic heterocycles like indoles and pyrroles is reported by a Pd nanocatalyst under ligand- and Cu-free conditions. The reaction conditions tolerate several functional groups and work very efficiently for aryl iodides and bromides. Aryl chlorides are also successful as the coupling partners albeit with lower yields. The methodology is also applicable for theN-arylation of aliphatic primary amines as demonstrated by the reactions of benzylamine with several aryl iodides as well as bromides. The recyclable Pd nanocatalyst catalyzes the reaction by a heterogeneous mechanism, which has been demonstrated by several techniques including the three phase test and thein situICP-MS analysis of the reaction mixture.
Design, synthesis, and evaluation of the antimycobacterial activity of 3-mercapto-1,2,4-triazole–pyrrole hybrids
Roman, Gheorghe,Bost?naru, Andra-Cristina,N?stas?, Valentin,Mare?, Mihai
, p. 531 - 546 (2019/10/02)
A series of 3-mercapto-1,2,4-triazole–pyrrole hybrids was designed as antimycobacterial agents by employing 5-(4-(1H-pyrrol-1-yl)phenyl)-4H-1,2,4-triazole-3-thiol as the scaffold onto which several types of moieties were introduced in the triazole ring at N-4 and N-2 and as substituents of the mercapto function. The aforementioned moieties are an allyl or a phenyl moiety at N-4; an aminomethyl group at N-2; or methyl, substituted benzyl, ethoxycarbonylmethyl, or substituted phenacyl at sulfur. Investigation of the compounds in the resulting library as growth inhibitors of Mycobacterium smegmatis showed that their minimum inhibitory concentration was higher than 64 mg/L.
Direct Arylation of α-Amino C(sp3)-H Bonds by Convergent Paired Electrolysis
Ma, Yueyue,Yao, Xiantong,Zhang, Lei,Ni, Pufan,Cheng, Ruihua,Ye, Jinxing
supporting information, p. 16548 - 16552 (2019/11/03)
A metal-free convergent paired electrolysis strategy to synthesize benzylic amines through direct arylation of tertiary amines and benzonitrile derivatives at room temperature has been developed. This TEMPO-mediated electrocatalytic reaction makes full use of both anodic oxidation and cathodic reduction without metals or stoichiometric oxidants, thus showing great potential and advantages for practical synthesis. This convergent paired electrolysis method provides a straightforward and powerful means to activate C?H bonds and realize cross-coupling with cathodically generated species.
Palladium catalysed aryl amination reactions in supercritical carbon dioxide
Smith, Catherine J.,Tsang, Melanie W.S.,Holmes, Andrew B.,Danheiser, Rick L.,Tester, Jefferson W.
, p. 3767 - 3781 (2007/10/03)
Palladium catalysed C-N bond formation in supercritical carbon dioxide has been accomplished. Carbamic acid formation is avoided in part through the use of an N-silylamine as the coupling partner. Employing a catalyst system of Pd 2dba3 (1 mol%) and 2-dicyclohexylphosphino-2′, 4′,6′-triisopropyl-1,1′-biphenyl (X-Phos) (2 mol%) enabled the catalytic amination of aryl bromides and chlorides with N-silylanilines to be realised in excellent yield. Extension of the methodology to the N-arylation of N-silyldiarylamines, N-silylazoles and N-silylsulfonamides is reported. The Royal Society of Chemistry 2005.
METHODS OF AMINATION
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Page/Page column 29, (2010/02/14)
A method of synthesising a compound of formula I: comprising the step of reacting a moiety of formula II: with a moiety of formula III: in compressed carbon dioxide in the presence of a transition metal catalyst and a base, wherein L is a labile leaving group; RN1 is optionally substituted C5-20 aryl; RN2is selected from optionally substituted C5-20aryl, optionally substituted C3-20 heterocyclyl, optionally substituted C3-7 alkyl, and optionally substituted sulfonyl; RN3 is selected from H and optionally substituted C1-7 alkyl, C3-20 heterocyclyl and C5-20aryl; or RN2 and RN3 together with the nitrogen atom to which they are attached form optionally substituted nitrogen-containing C3-20heterocylyl or C5-20 heteroaryl; and R1 R2 and R3 are independently selected from optionally substituted C1-7alkyl, C5-20 aryl, C3-20 heterocyclyl, hydroxy, halo, amino and C1-7 alkoxy, or two of R1, R2 and R3, together with the silicon atom to which they are attached, may form a silicon containing C5-7 heterocyclyl group.
FUSED HETEROCYCLIC COMPOUNDS, HAVING ANGIOTENSIN II ANTAGONISTIC ACTIVITY
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, (2008/06/13)
Fused heterocyclic compounds of the formula (I): STR1 wherein R. sup.1 is an optionally substituted hydrocarbon residue which may be attached through a hetero atom; R 2 is a group capable of forming an anion or a group convertible thereinto; R 3 is an optionally substituted aromatic hydrocarbon or heterocyclic residue which contains at least one hetero atom; X is a direct bond or a spacer having an atomic length of two or less between the R 3 group and the ring W group; W is an optionally substituted aromatic hydrocarbon or heterocyclic residue which contains at least one hereto atom; a,c and d are independently selected from the group consisting of one or two optionally substituted carbon atoms and one or two optionally substituted hetero atoms; b and e are independently selected from the group consisting of one optionally substituted carbon atom and one optionally substituted nitrogen atom wherein one of b or e must be nitrogen; the dotted line is a bond to form one double bond; n is an integer of 1 or 2 and when a, which is an optionally substituted carbon atom, is taken together with R 1, the following group: STR2 may form a ring group; provided that when STR3 is a benzimidazole, thieno[3,4-d] imidazole, or thieno[2,3-d] imidazole ring, at least one of the group: STR4 and R 3 is an optionally substituted heterocyclic residue; and the pharmaceutically acceptable salts thereof, have potent angiotensin II antagonistic activity and antihypertensive activity, thus being useful as therapeutic agents for treating circulatory system diseases such as hypertensive diseases, heart diseases (e.g. hypercardia, heart failure, cardiac infarction, etc.), strokes, cerebral apoplexy, nephritis, etc.
PHOTOCHEMISTRY OF 3,6-DIHYDRO-1,2-OXAZINES: A VERSATILE ROUTE TO SUBSTITUTED PYRROLES
Givens, R. S.,Choo, D. J.,Merchant, S. N.,Stitt, R. P.,Matuszewski, B.
, p. 1327 - 1330 (2007/10/02)
A high yield pyrrole synthesis which employs a sequence of cycloaddition, photoextrusion of H2O and Birch reduction has been developed.
