312753-94-9Relevant academic research and scientific papers
DIRECT STEREOSPECIFIC SYNTHESIS OF UNPROTECTED AZIRIDINES FROM OLEFINS
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, (2015/07/16)
A method for the direct stereospecific conversion of structurally diverse mono-, di-, tri- and tetra-substituted olefins to N-H, N-alkyl, N-cycloalkyl, or N-aralkyl aziridines using a hydroxylamine amination agent with transition metal catalyst. The method is operationally simple (i.e., one-pot), scalable and fast at ambient temperature.
Direct stereospecific synthesis of unprotected N-H and N-Me aziridines from olefins
Jat, Jawahar L.,Paudyal, Mahesh P.,Gao, Hongyin,Xu, Qing-Long,Yousufuddin, Muhammed,Devarajan, Deepa,Ess, Daniel H.,Kurti, Laszlo,Falck, John R.
, p. 61 - 65 (2014/03/21)
Despite the prevalence of the N-H aziridine motif in bioactive natural products and the clear advantages of this unprotected parent structure over N-protected derivatives as a synthetic building block, no practical methods have emerged for direct synthesis of this compound class from unfunctionalized olefins. Here, we present a mild, versatile method for the direct stereospecific conversion of structurally diverse mono-, di-, tri-, and tetrasubstituted olefins to N-H aziridines using O-(2,4-dinitrophenyl)hydroxylamine (DPH) via homogeneous rhodium catalysis with no external oxidants. This method is operationally simple (i.e., one-pot), scalable, and fast at ambient temperature, furnishing N-H aziridines in good-to-excellent yields. Likewise, N-alkyl aziridines are prepared from N-alkylated DPH derivatives. Quantum-mechanical calculations suggest a plausible Rh-nitrene pathway.
An investigation into the structure-activity relationships associated with the systematic modification of the β2-adrenoceptor agonist indacaterol
Beattie, David,Beer, David,Bradley, Michelle E.,Bruce, Ian,Charlton, Steven J.,Cuenoud, Bernard M.,Fairhurst, Robin A.,Farr, David,Fozard, John R.,Janus, Diana,Rosethorne, Elizabeth M.,Sandham, David A.,Sykes, David A.,Trifilieff, Alexandre,Turner, Katharine L.,Wissler, Elke
, p. 6280 - 6285 (2012/10/30)
The synthesis of a series of indacaterol analogues in which each of the three structural regions of indacaterol are modified in a systematic manner is described. Evaluation of the affinity of these analogues for the β2-adrenoceptor identified t
Beta2-adrenoceptor agonists
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Page/Page column 20, (2008/06/13)
Compounds of formula in free or salt or solvate form, where Ar is a group of formula Y is carbon or nitrogen and R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, X, n, p, q and r are as defined in the specification, their preparation and their use as pharmaceuticals, particularly for the treatment of obstructive or inflammatory airways diseases.
Redox-photosensitized aminations of 1,2-benzo-1,3-cycloalkadienes, arylcyclopropanes, and quadricyclane with ammonia
Yasuda, Masahide,Kojima, Ryuji,Tsutsui, Hiroshi,Utsunomiya, Daigo,Ishii, Kazuaki,Jinnouchi, Koutaro,Shiragami, Tsutomu
, p. 7618 - 7624 (2007/10/03)
1,2,4-Triphenylbenzene and 2,2′-methylenedioxy-1,1′ -binaphthalene successfully photosensitized the aminations of 1,2-benzo-1,3-cycloalkadienes, arylcyclopropanes, and quadricyclane with ammonia and primary amines in the presence of m- or p-dicyanobenzene, which gave the 4-amino-1,2-benzocycloalkenes, 3-amino-1-arylpropanes, and 7-amino-5-(p-cyanophenyl)bicyclo[2.2.1]hept-2-ene, respectively. A key pathway for the photosensitized amination is the hole transfer from the cation radicals of the sensitizers that were generated by photoinduced electron transfer to the electron acceptors to the substrates. Therefore, it was found that the relationships in oxidation potentials between the sensitizers and the substrates and the positive charge distribution of the cation radicals of the substrates were important factors for the efficient amination.
