A straightforward synthesis of indazolo[3,2-a]isoquinolin-6-amines
نویسندگان
چکیده
4-Substituted 1-bromoisoquinolin-3-amines were subjected to Suzuki coupling with o-nitrophenylboronic acid to yield 1-(2-nitrophenyl)isoquinolinamines, which participated in Cadogan cyclization with triethyl phosphite under microwave irradiation and pressure to yield fluorescent indazolo[3,2-a]isoquinolin-6-amines. The new compounds were also functionalized by transformation of the amino group.
منابع مشابه
Aryne [3 + 2] cycloaddition with N-sulfonylpyridinium imides and in situ generated N-sulfonylisoquinolinium imides: a potential route to pyrido[1,2-b]indazoles and indazolo[3,2-a]isoquinolines.
The aryne [3 + 2] cycloaddition process with pyridinium imides breaks the aromaticity of the pyridine ring. By equipping the imide nitrogen with a sulfonyl group, the intermediate readily eliminates a sulfinate anion to restore the aromaticity, leading to the formation of pyrido[1,2-b]indazoles. The scope and limitation of this reaction are discussed. As an extension of this chemistry, N-tosyli...
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