F
X.-F. Cui et al.
Letter
Synlett
pound E is oxidized by molecular oxygen to generate the
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.
target
phenyl(pyrrolo[1,2-a]quinoxalin-4-yl)methanone
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(3aa).
In summary, we have successfully developed a rutheni-
um(II)-catalyzed coupling-cyclization of 1-(2-aminophe-
nyl)pyrroles with sulfoxonium ylides.22 This new annula-
tion process uses a commercially available ruthenium cata-
lyst together with a free amino group as a traceless
directing group to permit alkenyl C–H functionalization
and to provide an efficient access to pyrrolo[1,2-a]quinox-
aline skeletons. The protocol not only is expeditious and
operationally simple, but also permits the use of a wide
range of substrates and has excellent tolerance to various
functional groups.
Supporting Information
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Chem. Int. Ed. 2017, 56, 13117.
(18) Hu, S.; Du, S.; Yang, Z.; Ni, L.; Chen, Z. Adv. Synth. Catal. 2019,
361, 3124.
Supporting information for this article is available online at
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References and Notes
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(22) Phenyl(pyrrolo[1,2-a]quinoxalin-4-yl)methanone
(3aa);
Typical Procedure
A Schlenk tube (20 mL) equipped with a stirrer bar was charged
with 1-(2-aminophenyl)pyrroles (1a; 0.2 mmol, 31.6 mg), sulf-
oxonium ylide 2a (0.3 mmol, 58.8 mg), [RuCl2(p-cymene)]2 (2.5
mol%, 3.1 mg), and AgNTf2 (20 mol%, 15.5 mg) under an air
atmosphere (1 atm). Anhyd tAmOH was added, and the mixture
was stirred at 100 °C for 12 h, then cooled to r.t. The mixture
was filtered through a short Celite pad, and the filtrate was con-
centrated. The residue was purified by column chromatography
[silica gel, PE–EtOAc–CHCl3 (8:1:1)] to give a yellow solid; yield:
71%.
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1H NMR (300 MHz, CDCl3): = 8.20–8.14 (m, 2 H), 8.04–7.99 (m,
2 H), 7.91 (d, J = 8.2 Hz, 1 H), 7.62 (m, 2 H), 7.49 (m, 3 H), 7.21 (d,
J = 4.1 Hz, 1 H), 6.96 (m, 1 H). 13C NMR (75 MHz, CDCl3): =
192.36, 149.90, 135.79, 134.73, 133.55, 131.06, 131.00, 129.40,
128.30, 127.92, 125.43, 124.34, 114.87, 114.72, 113.85, 108.86.
HRMS (ESI): m/z [M + H]+ calcd for C18H13N2O: 273.1023; found:
273.0939.
© 2020. Thieme. All rights reserved. Synlett 2020, 31, A–F