Research Progress on Construction of Heterocyclic Skeletons Based on α-Hydride Transfer Strategy

doi:10.6023/cjoc202212036

Abstract

The efficient construction of heterocyclic compounds is an important topic in the field of organic synthesis. [m＋n] cyclization reaction can form privilege molecules from the combination of two readily available reaction substrates, which is an important means for construction of cyclic skeletons. The [m＋n] cyclization reaction based on hydride transfer strategy can in situ generate hydride acceptor from two relatively simple substrates, avoiding the prefabrication of reaction substrates, which features high atom and step economy. In this review, the [m＋n] cyclization reactions based on hydride transfer strategy are selected as the research object. Starting from the framework of aza- and oxa-heterocycles constructed by this kind of reaction, this review is classified according to the size of the generated aza- and oxa-heterocycles. The recent progress of [m＋n] cyclization based on hydride transfer strategy since 2018 is summarized, and the development of this field is also prospected.

Key words: heterocyclic compounds, hydride-transfer strategy, [m＋n] cyclization

Cite this article

Yuzhuo Chen, Hongmei Sun, Liang Wang, Fangzhi Hu, Shuaishuai Li. Research Progress on Construction of Heterocyclic Skeletons Based on α-Hydride Transfer Strategy[J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2323-2337.

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Fig. & Tab. 19

Scheme 1. Highly efficient construction of heterocycles via hydride transfer/cyclization strategy

Scheme 2. Formal [5＋1] cyclization via hydride transfer strategy

Scheme 3. Formal [5＋1] cyclization with 2-methylindolenines as one-atom carbon synthons

Scheme 4. Formal [5＋1] cyclization with α-methyl-N-sulfonyl imines as one-atom carbon synthons

Scheme 5. Formal [5＋1] cyclization with 2-(1-phenylethylidene)malononitriles as one-atom carbon synthons

Scheme 6. Formal [5＋1] cyclization with 4-hydroxycoumarin as one-atom carbon synthon

Scheme 7. Formal [5＋1] cyclization with the nitrogen of amino acids as one-atom nitrogen synthons

Scheme 8. Formal [5＋1] cyclization with oxindoles as one-atom carbon synthons

Scheme 9. Formal [5＋1] cyclization with acyclic nucleophiles with active methylene as one-atom carbon synthons

Scheme 10. Formal [5＋1] cyclization with C4-amine-substituted isatins as five-atom synthons

Scheme 11. Formal [5＋1] dearomatization-cyclization with electron-rich phenols as one-atom carbon synthons

Scheme 12. Formal [5＋1] dearomatization-cyclization with 4-hydroxyindoles as one-atom carbon synthons

Scheme 13. Formal [5＋1] dearomatization-cyclization with O-alkyl ortho-oxybenzaldehydes as five-atom synthons

Scheme 14. Representative pharmaceutical molecules containing seven-membered aza-heterocycles

Scheme 15. Formal [5＋2] cyclization with aminomalonate as two-atom synthons

Scheme 16. Formal [5＋2] cyclization with 3-substituted indoles as two-atom synthons

Scheme 17. Formal [5＋2] cyclization with indoles as two-atom carbon synthons

Scheme 18. Formal [6＋1] cyclization with isatins as one-atom carbon synthons

Scheme 19. Application of hydride transfer strategy in construction of quinolinone

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