Eight-membered and larger rings DOI
Charles N. Moorefield, George R. Newkome

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 497 - 517

Published: Jan. 1, 2024

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

Illya Zalessky,

Jack M. Wootton, Jerry K. F. Tam

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(8), P. 5702 - 5711

Published: Feb. 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.

Language: Английский

Citations

11
Synthesis and Elaboration of Medium-Sized Ring Building Blocks Prepared via Cascade Ring Expansion Reactions DOI Creative Commons

Haimei Zhou,

Peter O’Brien, William P. Unsworth

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 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.

Language: Английский

Citations

0
Accessing polyarene-fused ten-membered lactams via oxidative N-heterocyclic carbene (NHC)-catalyzed high-order [7 + 3] annulation DOI

Chen‐Chang Cui,

Shaoqing Shi, Luyao Wang

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110541 - 110541

Published: Oct. 1, 2024

Language: Английский

Citations

0
Ring Expansion Reactions via C-N Bond Cleavage in the Synthesis of Medium-sized Cycles and Macrocycles DOI Creative Commons
Viacheslav Lysenko, Kostiantyn Nazarenko, Aleksandr Kostyuk

et al.

Journal of organic and pharmaceutical chemistry, Journal Year: 2024, Volume and Issue: 22(2), P. 26 - 40

Published: Nov. 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.

Language: Английский

Citations

0
Eight-membered and larger rings DOI
Charles N. Moorefield, George R. Newkome

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 497 - 517

Published: Jan. 1, 2024

Citations

0