86386-72-3Relevant academic research and scientific papers
Intramolecular [2 + 2] and [4 + 2] Cycloaddition Reactions of Cinnamylamides of Ethenetricarboxylate in Sequential Processes
Yamazaki, Shoko,Sugiura, Hirotaka,Ohashi, Shinnosuke,Ishizuka, Keisuke,Saimu, Rina,Mikata, Yuji,Ogawa, Akiya
, p. 10863 - 10886 (2016/11/29)
Intramolecular [2 + 2] and [4 + 2] cycloaddition reactions of cinnamylamides of ethenetricarboxylate in sequential processes have been studied. Reaction of 1,1-diethyl 2-hydrogen ethenetricarboxylate and trans-cinnamylamines in the presence of EDCI/HOBt/Et3N led to pyrrolidine products in one pot, via intramolecular [2 + 2], [4 + 2], and some other cyclizations. The types of the products depend on the substituents on the benzene ring and the reaction conditions. Reaction of cinnamylamines without substituents on the benzene ring and with halogens and OMe on the para position at room temperature gave cyclobutane-fused pyrrolidines as major products via [2 + 2] cycloaddition. The reaction at 80 °C in 1,2-dichloroethane gave δ-lactone fused pyrrolidines as major products, probably via ring-opening of the cyclobutanes. Interestingly, reaction of 1,1-diethyl 2-hydrogen ethenetricarboxylate and cinnamylamines bearing electron-withdrawing groups such as NO2, CN, CO2Me, CO2Et, and CF3 on ortho and para positions in the presence of EDCI/HOBt/Et3N at room temperature or at 60-80 °C gave tetrahydrobenz[f]isoindolines via [4 + 2] cycloaddition as major products. DFT studies have been performed to explained the observed [2 + 2]/[4 + 2] selectivity.
Use of CaH2 as a reductive hydride source: Reduction of ketones and imines with CaH2/ZnX2 in the presence of a Lewis acid
Aida, Toshio,Kuboki, Norikatsu,Kato, Kenji,Uchikawa, Wataru,Matsuno, Chikashi,Okamoto, Sentaro
, p. 1667 - 1669 (2007/10/03)
A new combination reagent of CaH2/ZnX2 effectively reduced a variety of ketones and imines to the corresponding alcohols and amines, respectively, in the presence of a catalytic amount of a Lewis acid such as Ti(O-i-Pr)4, Al(O-i-Pr)3, B(O-i-Pr)3 and ZnF2. Published by Elsevier Ltd.
Bicyclic and tricyclic amines as modulators of chemokine receptor activity
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, (2008/06/13)
The present application describes modulators of CCR3 of formula (I): A—E—NR1—G??(I) or pharmaceutically acceptable salt forms thereof, useful for the prevention of inflammatory diseases such as asthma and other allergic diseases.
Substituted azabicycloheptane derivatives, their preparation and use
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, (2008/06/13)
Novel 3-azabicyclo[3.2.0]heptane derivatives of the formula STR1 in which R1 and R2 have the meanings stated in the description, and their preparation are described. The substances are intermediates for the preparation of drugs.
?-Allyl palladium methodology for selective deprotection of allylamines. Practical synthesis of secondary amines
Lemarie-Audoire, Sandrine,Savignac, Monique,Dupuis, Christophe,Genet, Jean Pierre
, p. 1157 - 1166 (2007/10/03)
The palladium-promoted deallylation of allylamines derived from primary and secondary amines is achieved with high to quantitative yield in the presence of 2-mercaptobenzoic acid as an allyl scavenger.This method was used for the sequential cleavage of diallylamines.A synthetic application of this procedure is presented in the preparation of secondary amines from diallylamines. - Keywords: allylamine; deallylation; sequential deprotection; ?-allyl palladium complexes; 2-mercaptobenzoic acid; substitution of amines
Selective deprotection of allyl amines using palladium
Lemaire-Audoire,Lemaire-Audoire, Sandrine,Savignac,Savignac, Monique,Genet,Genet, Jean Pierre,Bernard,Bernard, Jean-Marie
, p. 1267 - 1270 (2007/10/02)
Mono and diallylamines can be cleaved using Pdf(0) catalyst and 2-mercaptobenzoic acid as nucleophile. This methodology has been successfully used for the sequential deprotection of diallylamines. The yields of desallylation are good to quantitative.
Heterocyclisations radicalaires d'aminothiols ethyleniques. II - Etude de l'influence des substituants de la double liaison sur l'orientation de la cyclisation
Crozet, Michel P.,Kaafarani, Mustapha,Surzur, Jean-Marie
, p. 390 - 398 (2007/10/02)
Free radical initiation of N-allyl-2-aminothiols 1-6 bearing substituents on the double bond give a mixture of thiazolidines and thiomorpholines.The more substituted the double bond the higher is the ratio of thiomorpholine/thiazolidine.To rationalize the
