Application of 2-Aminopyridines in the Synthesis of Five- and Six-Membered Azaheterocycles

doi:10.6023/cjoc202104011

Abstract

2-Aminopyridine is a significant synthetic synthon, with unique dual nucleophilic structure. It can react with ketones, aldehydes, acids, multifunctional esters, halogenated aromatics and other compounds to synthesize five- and six-member azaheterocycles. In recent years, the cyclization reactions based on 2-aminopyridines have been under the spotlight. According to the different types of substrates, the research progress on the synthesis of imidazo[1,2-a]pyridines and pyrido[1,2-a]pyri- midines based on 2-aminopyridines in the past 5 years is reviewed, and its applications in organic synthesis methodology, drug synthesis and fluorescent probes are summarized. Furthermore, the development trend of green cyclization and its application based on 2-aminopyridines in the future are prospected.

Key words: 2-aminopyridine, imidazo[1,2-a]pyridine, pyrido[1,2-a]pyrimidine, azaheterocycle, C—N bond formation, retro- synthetic analysis

Cite this article

Qi Chen, Sihong Chen, Hanqing Wu, Xiaoqing Zeng, Weiqing Chen, Guoxing Sun, Zhaoyang Wang. Application of 2-Aminopyridines in the Synthesis of Five- and Six-Membered Azaheterocycles[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3482-3491.

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Fig. & Tab. 17

Scheme 1. Retrosynthetic analysis for the synthesis of imidazo[1,2-a]pyridine from 2-aminopyridine

Scheme 2. Plausible mechanism for the synthesis of 2-arylimi- dazo[1,2-a]pyridines from 2-aminopyridines and α-bromoaceto- phenones

Scheme 3. Microwave radiation-assisted synthesis of α-bromo- acetophenone and its condensation reaction with 2-aminopyridine

Scheme 4. Synthesis of imidazo[1,2-a]pyridines from 2-amino- pyridine via organic electrochemical method

Scheme 5. Synthesis of imidazo[1,2-a]pyridines from 2-amino- pyridines and propargyl aldehydes

Scheme 6. Simple scheme of the plausible mechanism for the synthesis of imidazo[1,2-a]pyridines from 2-aminopyridines, aromatic aldehydes and terminal alkynes

Scheme 7. Synthesis of imidazo[1,2-a]pyridine compounds from 2-aminopyridine and chloroacetic acid

Scheme 8. Cyclization reaction of imidazo[1,2-a]pyridines from 2-aminopyridines

Scheme 9. Plausible mechanism for the synthesis of 2-aryl-3-formylimidazo[1,2-a]pyridines from 2-aminopyridines and cinnamaldehydes

Scheme 10. Retrosynthetic analysis for the synthesis of pyrido[1,2-a]pyrimidines from 2-aminopyridines

Scheme 11. Synthesis of anti-kidney tumor drugs from 2-amino- pyridine type compound and diethyl malonate

Scheme 12. Synthesis of HCV inhibitor from 2-aminopyridine type compound and bis(2,4,6-trichlorophenyl) malonate

Scheme 13. Plausible mechanism for the synthesis of 4H- pyrido[1,2-a]pyrimidin-4-ones from 2-aminopyridines and ethyl acetoacetates

Scheme 14. Plausible mechanism for the synthesis of 2H-pyri- do[1,2-a]pyrimidin-2-ones from 2-aminopyridines and ethyl acetoacetates

Scheme 15. Plausible mechanism for the synthesis of 2H-pyri- do[1,2-a]pyrimidin-2-ones from 2-aminopyridines and α-hydro- xymethyl acrylates

Scheme 16. Synthesis of 3-acyl-4H-pyrido[1,2-a]pyrimidin- 4-imines from enaminones and 2-aminopyridines

Scheme 17. Cyclization reaction of pyrido[1,2-a]pyrimidine compounds from 2-aminopyridines

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