Solid-phase synthesis and chemical properties of 2-(2-amino/hydroxyethyl)-1-aryl-3,4-dihydropyrazino[1, 2-b]indazol-2-iums.
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.
Kocí
Jan
J
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA.
Krchnák
Viktor
V
D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D048289:Imidazolidines / Q000737:chemistry; D007097:Imines / Q000737:chemistry; D007191:Indazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011719:Pyrazines / Q000737:chemistry*
D048289:Imidazolidines; D007097:Imines; D007191:Indazoles; D011719:Pyrazines