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. 2019 Aug 4;24(15):2835.
doi: 10.3390/molecules24152835.

Alcohol Participates in the Synthesis of Functionalized Coumarin-Fused Pyrazolo[3,4- b]Pyridine from a One-Pot Three-Component Reaction

Wei Lin  1 , Cangwei Zhuang  2 , Xiuxiu Hu  2 , Juanjuan Zhang  3 , Juxian Wang  4
Affiliations

Alcohol Participates in the Synthesis of Functionalized Coumarin-Fused Pyrazolo[3,4- b]Pyridine from a One-Pot Three-Component Reaction

Wei Lin et al. Molecules. .

Abstract

A concise and efficient approach to synthesizing coumarin-fused pyrazolo[3,4-b]pyridine via silica sulfuric acid (SSA) catalyzed three-component domino reaction under microwave irradiation has been demonstrated. Participation of various alcohols in construction of coumarin derivatives has been described for the first time. Short reaction time, high yields, one-pot procedure, usage of eco-friendly catalyst, and solvent are the key features of this method.

Keywords: coumarin; pyrazolo[3,4-b]pyridine; silica sulfuric acid; synthesis.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
General structures of coumarin molecules possessing biological activity.
Figure 2
Figure 2
Biologically active compounds having pyrazolo[3,4-b]pyridine unit.
Scheme 1
Scheme 1
Synthesis of coumarino[4,3-d]pyrazolo[3,4-b]pyridine derivative 3a.
Scheme 2
Scheme 2
New multicomponent domino reactions.
Figure 3
Figure 3
Crystal structure of 7a.
Scheme 3
Scheme 3
Synthesis of coumarin-fused pyrazolo[3,4-b]pyridine derivatives 7 a. a Reaction conditions: arylbenzo[f]chromen-3-one 4 (0.5 mmol), enaminone 2 (0.5 mmol), alkyl alcohol 5 (1.0 mL), EG (3 mL) and SSA (0.25 g), 140 °C,45 min; b Isolated yield; c 2 h.
Scheme 4
Scheme 4
Preliminary mechanistic studies. (A) Synthesis of coumarin-fused pyrazolo[3,4-b]pyridine derivatives 9a. (B) Synthesis of coumarin-fused pyrazolo[3,4-b]pyridine derivatives 7c. (C) Reaction of phenylmethanol with the catalyst of SSA.
Scheme 5
Scheme 5
Proposed mechanism for this reaction.
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