Work

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

Year: 2009

Type: article

Abstract: 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.

Source: Journal of Combinatorial Chemistry

DOI: 10.1021/cc9001422

Authors: Jan Kočí, Viktor Krchňák

Institution: University of Notre Dame

Language: English

Topic: Chemical Synthesis and Analysis

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: G1242290637, Diversity oriented combinational synthesis of bisheterocyclic libraries