Electrophilic and Nucleophilic Substitutions of 2-Amino- and 2-Hydroxy-1,3-diazaazulenes

Article abstract of DOI:10.1246/bcsj.61.2690

2-Amino (2) and 2-hydroxy-1,3-diazaazulenes (3) underwent smoothly electrophilic bromination under basic conditions to give 2-amino-4,6,8-tribromo- (4) and 6-bromo-2-hydroxy-1,3-diazaazulenes (7), respectively.Bromo derivatives 4 and 7 underwent some nucleophilic substitutions, e.g., 4 reacted with ease with sodium methoxide to give 2-amino-4,6,8-trimethoxy-1,3-diazaazulene (10).