Combining the diaza-diels-alder reaction and palladium-catalyzed aminations to prepare amino-substituted porphyrins
作者： Mean See Goh , Michael C. Pfrunder , John C. McMurtrie , Dennis P. Arnold
关键词: Anthracene 、 Diels–Alder reaction 、 Palladium 、 Diene 、 Organic chemistry 、 Catalysis 、 Amination 、 Medicinal chemistry 、 Chemistry 、 Autoxidation 、 Hydrolysis
摘要: A strategy to tackle the synthesis of azoporphyrins with unsubstituted terminal meso positions was investigated. It comprised combination diaza-Diels–Alder (DADA) reaction 1,3-dienes dialkyl azodicarboxylates, decarboxylative hydrolysis bis(carbamates), palladium-catalyzed amination bromoporphyrin precursors, and retro-DADA reactions release ultimate targets. The somewhat confused historical results on DADA 1,3-cyclohexadiene were clarified, but hydrolyses yielded extremely air-sensitive amines which decomposed completely in minutes via autooxidation reaction. With anthracene or 2,3-dimethyl-1,3-butadiene as diene, azoporphyrin not achieved three amino-substituted porphyrins obtained moderate yields under mild conditions. X-ray crystal structures several intermediates final aminoanthracene-porphyrin nickel(II) complex determined.
uq.edu.au
core.ac.uk参考文章(49)
정진후, 임선희, 손창국, 이왕근, Oxidative Decomposition of Di-tert-butyl azodicarboxylate and Ab Initio Studies on Fragmentation Mechanism Bulletin of The Korean Chemical Society. ,vol. 19, pp. 792- 794 ,(1998)
J.E. Anderson, J.M. Lehn, NMR Studies of rate processes and conformations—IX: Conformational rate processes in bridged bicyclic tetrahydropyridazine and piperidazine systems Tetrahedron. ,vol. 24, pp. 123- 135 ,(1968) , 10.1016/0040-4020(68)89015-5
G. Desimoni, G. Faita, P.P. Righetti, L. Toma, Solvent effect as the result of frontier molecular orbital interaction. V. Diels-Alder with heterodienophiles: a unified approach to the solvent effect of the Diels-Alder reactions Tetrahedron. ,vol. 46, pp. 7951- 7970 ,(1990) , 10.1016/S0040-4020(01)90093-6
Otto Diels, Susanne Schmidt, Wilhelm Witte, Zur Kenntnis der Dien‐Synthesen, XXXII. Mitteil.: Anthracen und Azodicarbonsäure‐ester European Journal of Inorganic Chemistry. ,vol. 71, pp. 1186- 1189 ,(1938) , 10.1002/CBER.19380710609
Angela Altomare, Maria Cristina Burla, Mercedes Camalli, Giovanni Luca Cascarano, Carmelo Giacovazzo, Antonietta Guagliardi, Anna Grazia Giuseppina Moliterni, Giampiero Polidori, Riccardo Spagna, SIR97: a new tool for crystal structure determination and refinement Journal of Applied Crystallography. ,vol. 32, pp. 115- 119 ,(1999) , 10.1107/S0021889898007717
John M. Mellor, Neil M. Smith, Reductive cleavage of the nitrogen–nitrogen bond in hydrazine derivatives Journal of The Chemical Society-perkin Transactions 1. ,vol. 16, pp. 2927- 2931 ,(1984) , 10.1039/P19840002927
Jørn B. Christensen, Lars Henriksen, Theis I. Sølling, A concerted mechanism for uncatalysed transfer of carbon substituents from diimides to CC and CC Organic and Biomolecular Chemistry. ,vol. 6, pp. 440- 442 ,(2008) , 10.1039/B717899A
Otto Diels, Jacob Hansen Blom, Werner Koll, Über das aus Cyclopentadien und Azoester entstehende Endomethylen-piperidazin und seine Überführung in 1,3-Diamino-cyclopentan Justus Liebigs Annalen der Chemie. ,vol. 443, pp. 242- 262 ,(1925) , 10.1002/JLAC.19254430112
Norbert Rieber, James Alberts, James A. Lipsky, David M. Lemal, .DELTA.1-1,2-Diazetines Journal of the American Chemical Society. ,vol. 91, pp. 5668- 5669 ,(1969) , 10.1021/JA01048A056
Wang Cun-Xiao, Robert S. Sheridan, Synthesis and reaction of 2,3-diazabicyclo[2.2.1]hept-5-ene Tetrahedron Letters. ,vol. 34, pp. 5673- 5676 ,(1993) , 10.1016/S0040-4039(00)73830-5