Categories: Synthesis of N-Heterocycles > benzo-fused N-Heterocycles >
Synthesis of isoquinolin-3-ones
Recent Literature
In rhodium-catalyzed C-H activation/annulation reactions for the synthesis of
sixteen 3,4-unsubstituted isoquinolones, vinyl acetate emerges as a convenient
acetylene equivalent. The complementary regiochemical preferences of enol ethers
versus enol esters/enamides is discussed.
N. J. Webb, S. P. Marsden, S. A. Raw, Org. Lett.,
2014,
16, 4716-4721.
A Co(III)-catalyzed redox-neutral annulation of benzamides and acrylamides
with vinylene carbonate provides isoquinolinones and pyridinones in very good
yields. This protocol tolerates diverse functional groups and substitution
patterns.
X. Li, T. Huang, Y. Song, Y. Qi, L. Li, Y. Li, Q. Xiao, Y. Zhang,
Org. Lett., 2020, 22, 5925-5930.
KOtBu-promoted SNAr reaction of 2-halobenzonitriles with
ketones followed by Cu(OAc)2-catalyzed cyclization gives isoquinolone
derivatives in good yields.
M. S. Mayo, X. Yu, X. Feng, Y. Yamamoto, M. Bao, J. Org. Chem.,
2015,
80, 3998-4002.
The isoquinolone scaffold can be arylated using aryliodonium salts as the
coupling partners at either the C4 or C8 position. The C4-selective arylation
was successfully achieved via an electrophilic palladation pathway, whereas an
Ir(III) catalytic system resulted in C-C bond formation exclusively at the C8
position.
S. Lee, S. Mah, S. Hong, Org. Lett.,
2015,
17, 3864-3867.
The isoquinolone scaffold can be arylated using aryliodonium salts as the
coupling partners at either the C4 or C8 position. The C4-selective arylation
was successfully achieved via an electrophilic palladation pathway, whereas an
Ir(III) catalytic system resulted in C-C bond formation exclusively at the C8
position.
S. Lee, S. Mah, S. Hong, Org. Lett.,
2015,
17, 3864-3867.
A palladium-catalyzed C(sp2)-H allylation/aminopalladation/β-H
elimination/isomerization sequence enables an annulation reaction of N-sulfonyl
amides and allylbenzenes to construct isoquinolinones and pyridinones in good
yield in the presence of air as the terminal oxidant.
R. Zhong, Y. Xu, M. Sun, Y. Wang, J. Org. Chem., 2021, 86,
5255-5264.
A Rh-catalyzed redox-neutral annulation of primary benzamides with diazo
compounds provides isoquinolinones. This efficient and economic procedure
exhibited good functional group tolerability, scalability, and regioselectivity,
obviating the need for oxidants, and only environmentally benign N2
and H2O were released.
Y. Wu, P. Sun, K. Zhang, T. Yang, H. Yao, A. Lin, J. Org. Chem.,
2016,
81, 2166-2173.
Rh(III)-catalyzed coupling of N-Boc hydrazones/N-Boc hydrazines
with diazodiesters/diazoketoesters provides convenient access to synthetically
and medicinally important N-amino isoquinolin-3-ones and N-amino
indoles via a C-H activation-based strategy.
P. Shi, L. Wang, S. Guo, K. Chen, J. Wang, J. Zhu, Org. Lett.,
2017, 19, 4359-4362.