Categories: Synthesis of N-Heterocycles > benzo-fused N-Heterocycles >
Synthesis of isoindoles
Recent Literature
A Rh-catalyzed intramolecular condensation of the benzyl azides with
α-aryldiazoesters provides isoindoles in very good yields. The reaction
proceeded through nucleophilic attack of the organic azide onto a rhodium
carbenoid, release of nitrogen gas, and tautomerization of an intermediate
imino esters.
J. Zhu, R. Li, Y. Su, P. Gu, J. Org. Chem., 2019, 84,
5813-5820.
A Rh(III)-catalyzed coupling of N-chloroimines with
α-diazo-α-phosphonoacetates enables an efficient dechlorinative/dephosphonative
access to 2H-isoindoles. In addition, a Ni(II)-catalyzed deesterification
enables the complete elimination of reactivity-assisting groups.
B. Qi, L. Li, Q. Wang, W. Zhang, L. Fang, J. Zhu,
Org. Lett., 2019, 21, 6860-6863.
α-Azido carbonyl compounds bearing a 2-alkenylaryl moiety at the α-position are
promising precursors for synthesis of isoindole and isoquinoline derivatives via
1,3-dipolar cycloaddition of azides onto alkenes and 6π-electrocyclization of
N-H imine intermediates, respectively.
B. W.-Q. Hui, S. Chiba, Org. Lett., 2009,
11, 729-732.
A one-pot conversion of isoindolines to 1-arylisoindoles was established from
palladium-catalyzed cascade C-H transformations. A dehydrogenation of
isoindolines followod by C-H arylation of the isoindoles gives the desired
1-arylisoindoles in good yields.
T. Ohmura, A. Kijima, M. Suginome, Org. Lett., 2011,
13, 1238-1241.