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Synthesis of novel fused azecine ring systems through application of the tert-amino effect
Authors:Petra Dunkel  Attila Bényei  Péter Mátyus
Institution:a Department of Organic Chemistry, Semmelweis University, H?gyes Endre u. 7., H-1092 Budapest, Hungary
b Institute of Physical Chemistry, University of Debrecen, Egyetem tér 1., H-4010 Debrecen, Hungary
c Department of Pharmacy, Semmelweis University, H?gyes Endre u. 7., H-1092 Budapest, Hungary
Abstract:Novel fused azecine ring systems were synthesized via the microwave-assisted thermal isomerization of terphenyl or biphenyl-pyridazine compounds possessing a vinyl and a tert-amino group, through application of a new extension of the tert-amino effect. Substrates for the ring closure were prepared from ortho-dihalobenzene or pyridazinone by consecutive Suzuki couplings with ortho-sec-amino- and formylphenylboronic acids, followed by Knoevenagel condensation of the aldehydes obtained.
Keywords:tert-Amino effect  Regioselective Suzuki coupling  Microwave  Fused azecine ring systems
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