2-(2-氨基/羟乙基)-1-芳基-3,4-二氢吡嗪并[1,2-b]吲唑-2-鎓的固相合成及化学性质
Solid-phase synthesis and chemical properties of 2-(2-amino/hydroxyethyl)-1-aryl-3,4-dihydropyrazino[1, 2-b]indazol-2-iums.
作者信息
Kocí Jan, Krchnák Viktor
机构信息
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA.
出版信息
J Comb Chem. 2010 Jan-Feb;12(1):168-75. doi: 10.1021/cc9001422.
Amino alcohols, diamines, benzenesulfonyl chlorides, and bromoketones were used to prepare polymer-supported 2-(2-(2-(amino/hydroxyl)ethylamino)ethyl)-3-benzoyl-2H-indazoles. Acid-mediated release yielded 2-((amino/hydroxyl)ethyl)-1-aryl-3,4-dihydropyrazino[1,2-b]indazole-2-iums. In neutral pH, iminiums spontaneously cyclized to complex fused heterocycles 3,6,9,10-tetraazatetracyclo[7.7.0.0(2,6).0(11,16)]hexadeca-11,13,15-trienes, 3-oxa-6,9,10-triazatetracyclo[7.7.0.0(2,6).0(11,16)]hexadeca-11,13,15-trienes, and 3,7,10,11-tetraazatetracyclo[8.7.0.0(2,7).0(12,17)]heptadeca-12,14,16-trienes. Transformations were carried out under mild conditions and tolerated diverse substitution patterns.
氨基醇、二胺、苯磺酰氯和溴代酮被用于制备聚合物负载的2-(2-(2-(氨基/羟基)乙基氨基)乙基)-3-苯甲酰基-2H-吲唑。酸介导释放产生2-((氨基/羟基)乙基)-1-芳基-3,4-二氢吡嗪并[1,2-b]吲唑-2-鎓盐。在中性pH值下，亚胺鎓盐自发环化形成复杂的稠合杂环3,6,9,10-四氮杂四环[7.7.0.0(2,6).0(11,16)]十六碳-11,13,15-三烯、3-氧杂-6,9,10-三氮杂四环[7.7.0.0(2,6).0(11,16)]十六碳-11,13,15-三烯和3,7,10,11-四氮杂四环[8.7.0.0(2,7).0(12,17)]十七碳-12,14,16-三烯。转化反应在温和条件下进行，并且能耐受多种取代模式。
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