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. 2022 Feb 17;12(10):5919-5927.
doi: 10.1039/d1ra07438e. eCollection 2022 Feb 16.

A multi pathway coupled domino strategy: I2/TBHP-promoted synthesis of imidazopyridines and thiazoles via sp3, sp2 and sp C-H functionalization

Yishou Wang  1 , Shichen Li  1 , Xinfeng Wang  1 , Yiming Yao  1 , Lei Feng  1 , Chen Ma  1
Affiliations

A multi pathway coupled domino strategy: I2/TBHP-promoted synthesis of imidazopyridines and thiazoles via sp3, sp2 and sp C-H functionalization

Yishou Wang et al. RSC Adv. .

Abstract

I2/TBHP-promoted, one-pot, multi pathway synthesis of imidazopyridines and thiazoles has been achieved through readily available ethylarenes, ethylenearenes and ethynearenes. I2/TBHP as an initiator and oxidant is used to realize the C-H functionalization of this domino reaction. Simple and available starting materials, wide range of functional group tolerance, high potential for drug activity of the products and application in production are the advantageous features of this method.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. The drugs and biologically active compounds containing imidazopyridines or thiazoles units.
Scheme 2
Scheme 2. Approach for the synthesis of imidazo[1,2-a]pyridine and thiazole.
Scheme 3
Scheme 3. Gram-scale synthesis of 3aa and 3ak. aReaction conditions: 1a (10 mmol), I2 (4 mmol), TBHP (30 mmol), 120 °C, 1 h 10 min then 2-aminopyridine (20 mmol), CuCl2 (5 mmol), solvent (20 mL), 110 °C, 4 h. bReaction conditions: 1a (2 mmol), 3a (2 mmol), 4a (2 mmol), I2 (2.4 mmol), TBHP (18 mmol), 120 °C, 1 h 20 min then 2-aminopyridine (12 mmol), CuCl2 (3 mmol), solvent (10 mL), 110 °C, 2.5 h. cReaction conditions: 1a (2 mmol), 3a (2 mmol), 4a (2 mmol), I2 (2.4 mmol), TBHP (18 mmol), 120 °C, 1 h 20 min then 2k (12 mmol), CuCl2 (3 mmol), solvent (10 mL), 110 °C, 2 h.
Scheme 4
Scheme 4. The control experiments.
Scheme 5
Scheme 5. The proposed reaction mechanism.
See this image and copyright information in PMC

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