Categories: Synthesis of N-Heterocycles >
Synthesis of isoquinolines
Recent Literature

Reaction of N-carbamoyl-functionalized enamine derivatives with benzyne
affords substituted indolines. An orthogonal reactivity is uncovered when
related enamine derivatives are modified as amides, such that isoquinolines are
formed as the product of condensation with benzyne.
C. D. Gilmore, K. M. Allan, B. M. Stoltz, J. Am. Chem. Soc., 2008,
130, 1558-1559.

Readily available 2-azido-3-arylacrylates react with α-diazocarbonyl compounds
and triphenylphosphine to furnish isoquinolines in good yields. The efficient
and general procedure involves a Wolff rearrangement, an aza-Wittig reaction,
and an electrocyclic ring closure.
Y.-Y. Yang, W.-G. Shou, Z.-B. Chen, D. Hong, Y.-G. Wang, J. Org. Chem., 2008,
73, 3928-3930.

The direct conversion of various amides to isoquinoline and β-carboline
derivatives via mild electrophilic amide activation, with
trifluoromethanesulfonic anhydride in the presence of 2-chloropyridine followed
by cyclodehydration upon warming provides the desired products with short
overall reaction times.
M. Movassaghi, M. D. Hill, Org. Lett., 2008,
10, 3485-3488.
