13880-55-2Relevant academic research and scientific papers
Reductive coupling of aromatic N,N-acetals using zinc and chlorotrimethylsilane
Hatano, Bunpei,Tachikawa, Tomoharu,Mori, Tetsunori,Nagahashi, Keita,Kijima, Tatsuro
supporting information; experimental part, p. 3467 - 3469 (2011/07/08)
The reductive coupling of aromatic N,N-acetals and N,O-acetal activated by chlorotrimethylsilane proceeded smoothly in the presence of zinc to give the corresponding diamines in good yields.
Zinc-mediated allylation and alkylation of aminals in the presence of TMSCl and diisopropylamine
Hatano, Bunpei,Nagahashi, Keita,Kijima, Tatsuro
supporting information; body text, p. 9188 - 9191 (2009/04/11)
(Chemical Equation Presented) An alkylation of aminals with organozinc reagents derived from allyl bromide, benzyl bromide, α-bromoacetate, and α-bromonitrile proceeded efficiently in the presence of TMSCl and diisopropylamine. This reaction system was applied to the synthesis of an antispasmodic: butaverine.
Towards phase-transfer catalysts with a chiral anion: Inducing asymmetry in the reactions of cations
Carter, Christabel,Fletcher, Sarah,Nelson, Adam
, p. 1995 - 2004 (2007/10/03)
The ability of chiral anions, for example bis[1,1′-bi-2-naphtholato]borate, to induce asymmetry in the reactions of prochiral cations was investigated. Ion-pairing of a borate anion with an aziridinium ion was demonstrated by NMR spectroscopy. The additio
A convenient direct synthesis of α-N,N-dialkylaminophosphonates under aprotic conditions
Malhiac, Catherine,Combret, Jean-Claude,Boussad, Kamal,Klein, Jean-Louis
, p. 299 - 301 (2007/10/03)
A general one-pot synthesis of N,N-dialkylaminophosphonates under aprotic conditions is proposed using aromatic, heteroaromatic or aliphatic aldehydes and N,N-dialkyl-aminosilanes under trimethylsilyltriflate catalysis.
SYNTHESE SELECTIVE DE 1,2,4,3-TRIAZAPHOSPHOLES SUBSTITUES EN 1,5. STRUCTURE CRISTALLINE MOLECULAIRE DU 1-METHYL-5-BENZYL-4-TRIFLUOROBORO-1,2,4,3-TRIAZAPHOSPHOLE
Haddad, M.,Legros, J. P.,Lopez, L.,Boisdon, M. T.,Barrans, J.
, p. 189 - 196 (2007/10/02)
A selective synthesis of 1,5-disubstituted 1,2,4,3-triazaphosphole 3 is described from bases of Schiff of 2-N substituted amidrazones 7.Crystalline molecular structure of a triazaphosphole complex with BF3 has been determinated by X-ray diffraction.Complexation occurs on N4 nitrogen atom. Key words: 1,2,4,3-triazaphospholes; ring contraction; 15N NMR; crystal structure.
SYNTHESIS AND SOME TRANSFORMATIONS OF 1-ARYL-2-AZA-1,3-BUTADIENES
Nikogosyan, L. L.,Nersesyan, K. A.,Satina, T. Ya.,Panosyan, G. A.,Indzhikyan, M. G.
, p. 671 - 675 (2007/10/02)
The synthesis of 1-aryl-2-aza-1,3-butadienes was realized by the alkaline cleavage of diethylmethyl(4-aryl-3-aza-3-butenyl)ammonium iodides or by the dehydrochlorination of 1-chloro-4-phenyl-3-aza-3-butene.They react with alcohol at the terminal vinyl group.The direction of reaction with amines depends to a large degree on the nature of the nucleophile.
Trimethylsilylamines III: mise en evidence du compose d'addition sur les aldehydes; preparation d'aminals et de β-dialkylamino β-arylesters en milieu aprotique
Aube, Philippe,Christot, Isabelle,Combret, Jean-Claude,Klein, Jean-Louis
, p. 1009 - 1014 (2007/10/02)
Dialkylaminotrimethylsilanes react with aromatic aldehydes using trimethylsilyltriflate and tetrabutylammonium fluoride as catalysts and lead quantitatively to the corresponding aminals in aprotic media.The intermediate silylated hemiaminal can be characterized in many cases, mainly with pyridinecarbaldehydes.Aminals are obtained from aliphatic aldehydes using fluoride ion as catalyst.A one-pot synthesis of some β-dialkylamino β-arylesters from these reagents is described.
211. Scope and Limitations of the Reductive Coupling of Aromatic Aldimine Derivatives with Formation of 1,2-Diarylethylenediamine Units, Using Low-Valent Titanium Reagents
Betschart, Claudia,Schmidt, Beat,Seebach, Dieter
, p. 1999 - 2021 (2007/10/02)
Besides the adducts from lithium amides to aromatic aldehydes, iminium salts, aminals, and N-silylimines of aromatic aldehydes are coupled by the black suspension obtained from TiCl4 and Mg turnings in tetrahydrofuran (THF).The 1,2-diarylethylenediamines with tertiary and primary amino groups thus obtained are formed with no or only moderate diastereoselectivity (products 4a-d (Scheme 2) and 5a-e (Scheme 3), respectively); the amine component may contain a strained ring or additional heteroatoms as in azetidin, bis(2-metoxyethyl)amine piperazine, morpholine, and thiomorpholine (products 6a-e; Table 1).By an in-situ procedure, ethylenediamines and propane-1,3-diamines with two secondary amino groups are cyclized with aromatic aldehydes to give exclusively trans-diaryl-substituted piperazine and perhydro-1,4-diazepine derivatives (products 7a-f; Table 2).Enantiomerically pure monocyclic trans,cis-5-alkyl-2,3-diaryl-piperazines and diazabicyclononanes and -decanes are obtained by employing suitable diamines prepared from the amino acids (S)-alanine, (S)-phenylalanine, (S)-proline, and from (S,S)- or (R,R)-cyclohexane-1,2-diamine, respectively (products 11a-i, 7e; Table 4).The configurations of all products are derived from the high-field NMR spectra, some of which are discussed in detail (Figs. 1 and 2, Tables 3 and 5); all new compounds are fully characterized by their physical data.Depending upon the structure of the components employed, the yields of purified products range from as low as 7percent to essentially quantitative.
STEREOCHEMISTRY OF AMINE-CATALYZED KNOEVENAGEL REACTIONS
Tanikaga, Rikuhei,Konya, Naoto,Kaji, Aritsune
, p. 1583 - 1586 (2007/10/02)
The amine-catalyzed Knoevenagel reactions of aldehydes and active methylene compounds containing two activating groups were found to involve many reversible steps, and the diastereomeric intermediary condensation compounds yielded thermodynamically stable products via carbanionic intermediates stablized and sterically affected by two activating groups.
