220130-49-4Relevant articles and documents
Mechanochemical lignin-mediated strecker reaction
Dabral, Saumya,Turberg, Mathias,Wanninger, Andrea,Bolm, Carsten,Hernández, José G.
, (2017/02/15)
A mechanochemical Strecker reaction involving a wide range of aldehydes (aromatic, heteroaromatic and aliphatic), amines, and KCN afforded a library of α-aminonitriles upon mechanical activation. This multicomponent process was efficiently activated by li
Mechanochemical Strecker Reaction: Access to α-Aminonitriles and Tetrahydroisoquinolines under Ball-Milling Conditions
Hernández, José G.,Turberg, Mathias,Schiffers, Ingo,Bolm, Carsten
supporting information, p. 14513 - 14517 (2016/10/03)
A mechanochemical version of the Strecker reaction for the synthesis of α-aminonitriles was developed. The milling of aldehydes, amines, and potassium cyanide in the presence of SiO2gave the corresponding α-aminonitriles in good to high yields. The high efficiency of the mechanochemical Strecker-type multicomponent reaction allowed the one-pot synthesis of tetrahydroisoquinolines after a subsequent internal N-alkylation reaction.
Lanthanide coordination polymer constructed from 2,2′-bipyridyl-4,4′-dicarboxylic acid: Structure, catalysis and fluorescence
Wang, Shengyan,Xu, Jianing,Zheng, Jifu,Chen, Xiaodong,Shan, Liang,Gao, Lijuan,Wang, Li,Yu, Miao,Fan, Yong
, p. 81 - 86 (2015/09/15)
Two new isostructural lanthanide coordination polymers (Ln-CPs) [Ln2(bpdc)3(DMF)2] (Ln = Tb for 1, Eu for 2) with two kinds of one-dimensional channels along the a axis, were synthesized by 2,2′-bipyridyl-4,4′-dicarboxylic acid (H2bpdc) under solvothermal conditions. With exposed Lewis acid Ln3+ centers, 1 as a heterogeneous catalyst shows good catalytic reactivity and selectivity for the Strecker reaction affording medium to excellent conversion yields. Luminescent studies illustrate that 1 and 2 show intensive green and red luminescence triggered by efficient antenna effect of ligands under UV light, respectively. Moreover, 1 exhibits sensitive fluorescent response to Cu2+ in DMF solution.
Synthesis of highly substituted 2-13c-imidazolium salts and metal NHC complexes for the investigation of electronic unsymmetry by NMR
Emsermann, Jens,Arduengo, Anthonyj.,Opatz, Till
, p. 2251 - 2264 (2013/09/02)
Complexes of unsymmetrically substituted N-heterocyclic carbenes with NMR-active metals (Ag, Hg, Pt) with or without a 13C-label in the 2-position were synthesized by aldimine cross coupling and analyzed with respect to the scalar couplings between the metal center or C2 and the other ring atoms. Georg Thieme Verlag Stuttgart. New York.
Asymmetric addition of trimethylsilylcyanide to N-benzylimines catalyzed by recyclable chiral dimeric V(V) salen complex
Khan, Noor-ul H.,Saravanan,Kureshy, Rukhsana I.,Abdi, Sayed H.R.,Sadhukhan, Arghya,Bajaj, Hari C.
experimental part, p. 1133 - 1137 (2010/06/13)
Chiral dimeric vanadium (V) salen complex (10 mol%) derived from 5,5-Methylene di-[(S,S)-{N-(3-tert-butyl salicylidine)-N′-(3′,5′-di-tert-butyl salicylidene)]-1,2-cyclohexanediamine] with vanadyl suphate followed by auto oxidation was used as efficient catalyst for enantioselective Strecker reaction of N-benzylimines with TMSCN at -30 °C. Excellent yield (92%) of α-aminonitrile and high chiral induction was achieved (ee up to 94%) in case of 2-methoxy substituted N-benzylimines in 10 h. The catalytic system worked well up to four cycles with retention of enantioselectivity.
Iminoheterocycles as γ-secretase modulators
Caldwell, John P.,Bennett, Chad E.,McCracken, Troy M.,Mazzola, Robert D.,Bara, Thomas,Buevich, Alexei,Burnett, Duane A.,Chu, Inhou,Cohen-Williams, Mary,Josein, Hubert,Hyde, Lynn,Lee, Julie,McKittrick, Brian,Song, Lixin,Terracina, Giuseppe,Voigt, Johannes,Zhang, Lili,Zhu, Zhaoning
scheme or table, p. 5380 - 5384 (2010/12/24)
The synthesis of a novel series of iminoheterocycles and their structure-activity relationship (SAR) as modulators of γ-secretase activity will be detailed. Encouraging SAR generated from a monocyclic core led to a structurally unique bicyclic core. Selected compounds exhibit good potency as γ-secretase modulators, excellent rat pharmacokinetics, and lowering of Aβ42 levels in various in vivo models.
SUBSTITUTED PHENYLCYCLOHEXANE CARBOXYLIC ACID AMIDES AND THEIR USE AS ADENOSINE UPTAKE INHIBITORS
-
Page/Page column 28-30, (2010/02/13)
The present invention relates to substituted phenylcyclohexanecaboxamides of the formula (I), to processes for their preparation and to their use in medicaments, in particular for treating cardiovascular disorders.
A facile synthesis of substituted phenylglycines
Davies, Antony J.,Ashwood, Michael S.,Cottrell, Ian F.
, p. 1095 - 1102 (2007/10/03)
A convenient scaleable process for the preparation of substituted phenylglycines 2 by a modified Strecker reaction is described. Bisulfite- mediated addition of benzylamine and cyanide anion to substituted benzaldehydes 3 gave the aminonitriles 4 which were hydrolysed in two steps to the N-protected amino acid 1. Debenzylation using catalytic transfer hydrogenation gave the title compounds in good yield.
Syntheses of optically active α-amino nitrites by asymmetric transformation of the second kind using a principle of O. Dimroth
Hassan, Nasser A.,Bayer, Erwin,Jochims, Johannes C.
, p. 3747 - 3757 (2007/10/03)
A mixture of solids As and Bs in equilibrium with the dissolved compounds A1 and B1 is transformed completely into one pure solid, say Bs, if the dissolved compounds A1?B1 are equilibrating in solution. This is applied to transform 1:1 mixtures of solid diastereomeric amygdalates (2-hydroxy-2-phenylacetates; mandelates) (R,R)-3 + (S,R)-3 prepared from racemic α-amino nitriles (R,S)-1 with (R)-mandelic acid 2 into stereochemically pure single diastereomers (R,R)-3, or (S,R)-3 (de > 97%) ('asymmetric transformation of the second kind by application of Dimroth's principle'). Decomposition of the amygdalates (R,R)-3, or (S,R)-3, with aqueous base affords the enantiomerically pure α-amino nitriles (A)-1, or (S)-1 (ten examples). The chiral auxiliary (R)-mandelic acid is recovered almost quantitatively. The optically active α-amino nitriles are hydrolyzed to amides 6, and further to α-N-alkylamino acids 7. N-Benzylamino acids 7 are hydrogenated to α-amino acids 8. Some of the optically active α-amino nitriles 1 are reduced to optically active 1,2-diamines 9. In most cases, absolute configurations could be assigned by comparison of the specific rotations observed with those of authentic compounds.
Synthesis of N-benzyl-3-(S)-(+)-(4-fluorophenyl)-1,4-oxazin-2-one via a crystallisation induced asymmetric transformation
Alabaster, Ramon J.,Gibson, Andrew W.,Johnson, Simon A.,Edwards, John S.,Cottrell, Ian F.
, p. 447 - 450 (2007/10/03)
The simple and efficient preparation of enantiomerically pure N-benzyl-3-(S)-(+)-(4-fluorophenyl)-1,4-oxazin-2-one by a crystallisation induced asymmetric transformation of its racemate is reported. A key feature of this process is the use of [(1S)-(endo,
