Strain-enabled radical spirocyclization cascades: rapid access to spirocyclobutyl lactones and – lactams DOI Creative Commons
Kousik Das,

Abhilash Pedada,

Tushar Singha

и другие.

Chemical Science, Год журнала: 2023, Номер 15(9), С. 3182 - 3191

Опубликована: Дек. 21, 2023

Two complementary strain-enabled radical spirocyclization cascades have been realized to synthesize spirocyclobutyl lactones and – lactams. The reactions operate under mild conditions demonstrate excellent functional group compatibility.

Язык: Английский

Multicomponent Synthesis of Alkyl BCP-Heteroaryls via Electron Donor–Acceptor Complex Photoactivation under Mild Conditions DOI
Yanhe Li, Jun Xu, Yuxin Wang

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер 90(4), С. 1683 - 1696

Опубликована: Янв. 17, 2025

In the vanguard of sustainable chemistry, pursuit efficient pathways for synthesis alkyl bicyclo[1.1.1]pentane-heteroaryls has captured attention scientific vanguard. We herein report a groundbreaking and eco-conscious multicomponent coupling reaction that paves way alkylation heteroarylation [1.1.1]propellane, process uniquely enabled by photochemical prowess an electron donor–acceptor (EDA) complex. This method is distinguished its minimalist yet powerful approach: devoid transition metals, additives, photosensitizers. Its universality further exemplified seamless compatibility broad spectrum halides heteroarenes under standardized conditions, heralding new era synthetic versatility. The method's practicality underscored capacity late-stage modification pharmaceuticals, offering transformative tool enhancement existing drug molecules. Moreover, facile derivatization synthesized products underscores adaptability potential diverse applications. Our mechanistic studies have elucidated underlying radical-relay pathway, pinpointing pivotal role EDA complex in initiating transformation. discovery not only enriches our fundamental understanding but also opens avenues strategic optimization.

Язык: Английский

Процитировано

6
A reagent to access methyl sulfones DOI Creative Commons

Yaroslav Poplavskyi,

Vasyl Ripenko,

Sergei Bova

и другие.

Nature Communications, Год журнала: 2025, Номер 16(1)

Опубликована: Янв. 29, 2025

A chemical reagent to access methyl sulfones has been developed. Its reaction with various bis-nucleophiles leads the rapid formation of previously unknown heteroaromatic sulfones. Analogous strategy can also be used construct alkyl-, CHF2-, CF3- and even bicyclo[1.1.1]pentane-containing derivatives. These compounds have demonstrated a high potential for use in medicinal chemistry coordination chemistry. Methyl sulfone is standard polar substituent found different agro chemicals or drugs but due lack convenient efficient approaches them, are less investigated. Here authors report

Язык: Английский

Процитировано

3
Rapid and Scalable Halosulfonylation of Strain‐Release Reagents** DOI Creative Commons
Helena D. Pickford, Vasyl Ripenko, Ryan E. McNamee

и другие.

Angewandte Chemie International Edition, Год журнала: 2022, Номер 62(3)

Опубликована: Окт. 13, 2022

Sulfonylated aromatics are commonplace motifs in drugs and agrochemicals. However, methods for the direct synthesis of sulfonylated non-classical arene bioisosteres, which could improve physicochemical properties drug agrochemical candidates, limited. Here we report a solution to this challenge: one-pot halosulfonylation [1.1.1]propellane, [3.1.1]propellane bicyclo[1.1.0]butanes that proceeds under practical, scalable mild conditions. The sulfonyl halides used chemistry feature aryl, heteroaryl alkyl substituents, conveniently generated situ from readily available sulfinate salts halogen atom sources. This methodology enables an array pharmaceutically agrochemically relevant halogen/sulfonyl-substituted bioisosteres cyclobutanes, on up multidecagram scale.

Язык: Английский

Процитировано

64
2-Oxabicyclo[2.2.2]octane as a new bioisostere of the phenyl ring DOI Creative Commons

Vadym V. Levterov,

Yaroslav Panasiuk,

Kateryna Sahun

и другие.

Nature Communications, Год журнала: 2023, Номер 14(1)

Опубликована: Окт. 2, 2023

The phenyl ring is a basic structural element in chemistry. Here, we show the design, synthesis, and validation of its new saturated bioisostere with improved physicochemical properties - 2-oxabicyclo[2.2.2]octane. design structure based on analysis advantages disadvantages previously used bioisosteres: bicyclo[1.1.1]pentane, bicyclo[2.2.2]octane, cubane. key synthesis step iodocyclization cyclohexane-containing alkenyl alcohols molecular iodine acetonitrile. 2-Oxabicyclo[2.2.2]octane core incorporated into Imatinib Vorinostat (SAHA) drugs instead ring. In Imatinib, such replacement leads to improvement properties: increased water solubility, enhanced metabolic stability, reduced lipophilicity. Vorinostat, results bioactive analog drug. This study enhances repertoire available bioisosteres (hetero)aromatic rings for use drug discovery projects.

Язык: Английский

Процитировано

35
Photoredox-Catalyzed Alkylarylation of N-Aryl Bicyclobutyl Amides with α-Carbonyl Alkyl Bromides: Access to 3-Spirocyclobutyl Oxindoles DOI
Jian-Hong Fan,

Jing Yuan,

Pengfei Xia

и другие.

Organic Letters, Год журнала: 2024, Номер 26(10), С. 2073 - 2078

Опубликована: Март 6, 2024

A visible-light-induced radical alkylarylation of N-aryl bicyclobutyl amides with α-carbonyl alkyl bromides for the synthesis functionalized 3-spirocyclobutyl oxindoles is described in which β-selective addition to forms a key intermediate followed by interception intrinsic arene functional group. This approach can be applicable wide range bromides, including primary, secondary, and tertiary α-bromoalkyl esters, ketones, nitriles, nitro compounds.

Язык: Английский

Процитировано

14
Transition-metal-, oxidant- and additive-free multi-component synthesis of alkyl heteroaryl BCPs enabled by visible-light-induced phosphine-catalyzed halogen-atom transfer DOI
Jun Xu,

Yu Hong,

Ruiyuan Xu

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

This study describes a pioneering visible-light-induced phosphine-catalyzed halogen-atom transfer (XAT) strategy that heralds new era in the difunctionalization of [1.1.1]propellane.

Язык: Английский

Процитировано

13
Pyridine-boryl radical-catalyzed [3π + 2σ] cycloaddition for the synthesis of pyridine isosteres DOI
Yuan Liu,

Shuang Lin,

Zhengwei Ding

и другие.

Chem, Год журнала: 2024, Номер unknown

Опубликована: Сен. 1, 2024

Язык: Английский

Процитировано

12
Synthesis of Heterocycle-Substituted Bicyclo[3.1.1]heptanes and Aza-bicyclo[3.1.1]heptanes via Photocatalytic Minisci Reaction DOI Creative Commons
Rebecca I. Revie,

Benjamin J. Whitaker,

Bhaskar Paul

и другие.

Organic Letters, Год журнала: 2024, Номер 26(14), С. 2843 - 2846

Опубликована: Янв. 22, 2024

A route toward heterocycle-functionalized bicyclo[3.1.1]heptanes (BCHeps) and aza-bicyclo[3.1.1]heptanes (aza-BCHeps) has been developed, using mild, photocatalytic Minisci-like conditions to introduce various heterocycles at the bridgehead position from readily available N-hydroxyphthalimide esters of corresponding carboxylic acids. This chemistry enables access BCHep-containing structures that are highly relevant in medicinal research as potential bioisosteres meta-substituted arenes pyridines.

Язык: Английский

Процитировано

10
(Bio)isosteres of ortho- and meta-substituted benzenes DOI Creative Commons
H Erik Diepers, Johannes C. L. Walker

Beilstein Journal of Organic Chemistry, Год журнала: 2024, Номер 20, С. 859 - 890

Опубликована: Апрель 19, 2024

Saturated bioisosteres of substituted benzenes offer opportunities to fine-tune the properties drug candidates in development. Bioisosteres

Язык: Английский

Процитировано

10
Iodopentafluorosulfanylation of [1.1.1]propellane and further functionalizations DOI
Xin Zhao,

Jia‐Yi Shou,

Feng‐Ling Qing

и другие.

Science China Chemistry, Год журнала: 2023, Номер 66(10), С. 2871 - 2877

Опубликована: Авг. 24, 2023

Язык: Английский

Процитировано

21