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. Author manuscript; available in PMC: 2019 May 14.
Published in final edited form as: Anal Chem. 2019 Feb 6;91(4):3110–3117. doi: 10.1021/acs.analchem.8b05709

Scheme 1.

Synthesis of Non-NIR Fluorescent Rosol Dyes and THQ-Rosol.a

Scheme 1.

aReagents and conditions: (a) 1, benzoyl chloride, AICI3, DCM, 0°C → RT; BBr3, DCM, 0°C → RT; Me-2 (89%), Et-2 (92%), Pip- 2 (94%), Jul-2 (27%); (b) 2, resorcinol, MeSO3H, 100°C, 3 hr, Me- Rosol (69%), Et-Rosol (8%), Pip-Rosol (25%), Jul-Rosol (4%); (c) 3, benzoyl chloride, AlCl3, DCM, 0°C → RT, 2 hr, N2, 85%; (d) 4, resorcinol, MeSO3H, 90°C, overnight, 49%.