Solid-Phase Synthesis and Chemical Properties of 2-(2-Amino/hydroxyethyl)-1-aryl-3,4-dihydropyrazino[1, 2-b]indazol-2-iums

被引：12
作者：
Koci, Jan [1 ]
Krchnak, Viktor [1 ]
机构：
[1] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA
来源：
JOURNAL OF COMBINATORIAL CHEMISTRY | 2010年 / 12卷 / 01期
关键词：
POLYMER-SUPPORTED SYNTHESIS; INTRAMOLECULAR CYCLIZATION; EFFICIENT SYNTHESIS; N-ACYLIMINIUM; HETEROCYCLES; DESIGN; IONS; RING;
D O I：
10.1021/cc9001422
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
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.
引用
收藏
页码：168 / 175
页数：8
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