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. Author manuscript; available in PMC: 2024 Oct 25.
Published in final edited form as: Tetrahedron Lett. 2023 Sep 9;130:154748. doi: 10.1016/j.tetlet.2023.154748

Table 2.

One-Pot Optimization Toward Fluorescent Pyrido-imidazo[4,5-c]isoquinolines

graphic file with name nihms-1936025-t0015.jpg
Entrya Acid (eq.) Solvent (0.3 M) Time (min) Yield (%)
1 Cu(OTf)2(1.0) MeOH 5 0
2 Cu(OTf)2(1.0) DCMb 20 0
3 Cu(OTf)2(1.0) ACN 20 0
4 - AcOH 20 28
5 H2SO4(30 eq.) AcOH 20 6
6 H2SO4(50 eq.) MeOH 20 0
7 H2SO4(50 eq.) MeOH 20, 5c 81
8 H2SO4(50 eq.) MeOH 20, 10c 87
9 H2SO4(50 eq.) MeOH 20, 20c 96
a

Scale: 1.0 mmol

b

100 °C

c

Acid was added after 1st indicated time and set to run for the 2nd indicated time at 140 °C (microwave irradiation).