A Modular Strategy for the Synthesis of Macrocycles and Medium-Sized Rings via Cyclization/Ring Expansion Cascade Reactions

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(8), С. 5702 - 5711

Опубликована: Фев. 19, 2024

Macrocycles and medium-sized rings are important in many scientific fields technologies but hard to make using current methods, especially on a large scale. Outlined herein is strategy by which functionalized macrocycles can be prepared cyclization/ring expansion (CRE) cascade reactions, without resorting high dilution conditions. CRE reactions designed operate exclusively via kinetically favorable 5–7-membered ring cyclization steps; this means that the problems typically associated with classical end-to-end macrocyclization avoided. A modular synthetic approach has been developed facilitate simple assembly of requisite linear precursors, then converted into an extremely broad range one nine protocols.

Язык: Английский

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Synthesis and Elaboration of Medium-Sized Ring Building Blocks Prepared via Cascade Ring Expansion Reactions

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 1, 2025

A general approach is described for the synthesis and elaboration of medium-sized ring mono- difunctionalized 8- or 9-membered lactone building blocks. The lactones are prepared via cascade expansion reactions elaborated Suzuki-Miyaura cross coupling various N-functionalization reactions. This enables efficient access to diverse, blocks in a synthetically challenging under-represented area pharmaceutical chemical space.

Язык: Английский

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Accessing polyarene-fused ten-membered lactams via oxidative N-heterocyclic carbene (NHC)-catalyzed high-order [7 + 3] annulation

Chinese Chemical Letters, Год журнала: 2024, Номер unknown, С. 110541 - 110541

Опубликована: Окт. 1, 2024

Язык: Английский

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Ring Expansion Reactions via C-N Bond Cleavage in the Synthesis of Medium-sized Cycles and Macrocycles

Journal of organic and pharmaceutical chemistry, Год журнала: 2024, Номер 22(2), С. 26 - 40

Опубликована: Ноя. 8, 2024

The literature review discusses and systematizes synthetic approaches to medium-sized cycles macrocycles based on ring expansion reactions of bi- or polycyclic systems via C-N bond cleavage. Ring bicyclic ammonium salts proceed thermal decomposition the action strong bases. Bi- containing a common amine group can be reduced with reducing reagents, e.g. lithium aluminum hydride. Ammonium derivatives are much more prone nucleophilic attack quite often used as starting materials for synthesis cycles. Bicyclic aminal amidine rings cleavage endocyclic bond. Various methods their activation reduction discussed in review.

Язык: Английский

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Eight-membered and larger rings

Progress in heterocyclic chemistry, Год журнала: 2024, Номер unknown, С. 497 - 517

Опубликована: Янв. 1, 2024

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