Six-membered ring systems: Diazines and benzo derivatives DOI

K. Alison Rinderspacher

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 355 - 393

Published: Jan. 1, 2024

Synthesis of polysubstituted bicyclo[2.1.1]hexanes enabling access to new chemical space DOI Creative Commons

Marius Reinhold,

Justin Steinebach,

Christopher Golz

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(36), P. 9885 - 9891

Published: Jan. 1, 2023

Crossed [2 + 2] cycloaddition yields bicyclo[2.1.1]hexanes with 11 different substitution patterns. ortho -, meta - and polysubstituted benzene bioisosteres, structures substituent patterns that go beyond aromatic chemical space can be prepared.

Language: Английский

Citations

47
Three-dimensional saturated C(sp3)-rich bioisosteres for benzene DOI
Jet Tsien, Chao Hu, Rohan R. Merchant

et al.

Nature Reviews Chemistry, Journal Year: 2024, Volume and Issue: 8(8), P. 605 - 627

Published: July 9, 2024

Language: Английский

Citations

44
Light‐Driven Synthesis and Functionalization of Bicycloalkanes, Cubanes and Related Bioisosteres DOI Creative Commons
Sara Cuadros, Julien Paut, Elsa Anselmi

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(14)

Published: Jan. 5, 2024

Bicycloalkanes, cubanes and their structural analogues have emerged as bioisosteres of (hetero)arenes. To meet increasing demand, the chemical community has developed a plethora novel synthetic methods. In this review, we assess progress made in field light-driven construction functionalization such relevant molecules. We focused on diverse targets, well reaction processes giving access to: (i) [1.1.1]-bicyclopentanes (BCPs); (ii) [2.2.1]-bicyclohexanes (BCHs); (iii) [3.1.1]-bicycloheptanes (BCHeps); (iv) cubanes; other structurally related scaffolds. Finally, future perspectives dealing with identification manifolds to new functionalized bioisosteric units are discussed.

Language: Английский

Citations

28
C–H functionalization of pyridines DOI

Susmita Maity,

Asish Bera,

Ayantika Bhattacharjya

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(28), P. 5671 - 5690

Published: Jan. 1, 2023

This review discusses known approaches for selective pyridine C–H editing, focusing on recent discoveries uniquely suited to pyridines.

Language: Английский

Citations

31
2‐Oxabicyclo[2.1.1]hexanes: Synthesis, Properties, and Validation as Bioisosteres of ortho‐ and meta‐Benzenes DOI Creative Commons

Vadym V. Levterov,

Yaroslav Panasiuk, Oleh Shablykin

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(19)

Published: March 11, 2024

Abstract We have developed a general and practical approach towards 2‐oxabicyclo[2.1.1]hexanes with two three exit vectors via an iodocyclization reaction. The obtained compounds been easily converted into the corresponding building blocks for use in medicinal chemistry. 2‐Oxabicyclo[2.1.1]hexanes incorporated structure of five drugs agrochemicals, validated biologically as bioisosteres ortho ‐ meta ‐benzenes.

Language: Английский

Citations

14
(Bio)isosteres of ortho- and meta-substituted benzenes DOI Creative Commons
H Erik Diepers, Johannes C. L. Walker

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 859 - 890

Published: April 19, 2024

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

Language: Английский

Citations

10
Selective P450BM3 Hydroxylation of Cyclobutylamine and Bicyclo[1.1.1]pentylamine Derivatives: Underpinning Synthetic Chemistry for Drug Discovery DOI Creative Commons
Lucy A. Harwood,

Ziyue Xiong,

Kirsten E. Christensen

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(50), P. 27767 - 27773

Published: Dec. 5, 2023

Achieving single-step syntheses of a set related compounds divergently and selectively from common starting material affords substantial efficiency gains when compared with preparing those same by multiple individual syntheses. In order for this approach to be realized, complementary reagent systems must available; here, panel engineered P450BM3 enzymes is shown fulfill remit in the selective C–H hydroxylation cyclobutylamine derivatives at chemically unactivated sites. The oxidations can proceed high regioselectivity stereoselectivity, producing valuable bifunctional intermediates synthesis applications fragment-based drug discovery. process also applies bicyclo[1.1.1]pentyl (BCP) amine achieve first direct enantioselective functionalization bridging methylenes open short efficient route chiral BCP bioisosteres medicinal chemistry. combination substrate, enzyme, reaction engineering provides powerful general platform small-molecule elaboration diversification.

Language: Английский

Citations

17
Recent Progress in Accessing Multi-functionalized Caged Hydrocarbons: En Route to Highly Functionalized Saturated (Bio)isosteres of Benzene Rings DOI
Shota Nagasawa, Yoshiharu Iwabuchi

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: July 4, 2024

Abstract Recently, many saturated bioisosteres of the benzene ring have been developed, and their applications in drug development evaluated. Most these are caged hydrocarbons, which rigid skeletons three-dimensional spaces. Recent efforts to synthesize hydrocarbons enabled access multi-functionalized congeners that expected be (bio)isosteres benzenes. This short review summarizes recently reported methods for obtaining (typically more than disubstituted) hydrocarbons. 1 Introduction 2 Proposed Structures Caged Hydrocarbons as Saturated (Bio)isosteres Benzene Ring: A Brief Summary 3 Access Multi-functionalized Hydrocarbons: De Novo Synthetic Approaches 3.1 Bicyclo[1.1.1]pentanes (BCPs) 3.2 Bicyclo[2.1.1]hexanes (BCHs) 3.3 Bicyclo[3.1.1]heptanes (BCHeps) 3.4 Others 4 C–H Functionalization 5 Conclusion

Language: Английский

Citations

7
Light-enabled scalable synthesis of bicyclo[1.1.1]pentane halides and their functionalizations DOI Creative Commons
Vasyl Ripenko, Vadym Sham, Vitalina Levchenko

et al.

Nature Synthesis, Journal Year: 2024, Volume and Issue: 3(12), P. 1538 - 1549

Published: Sept. 5, 2024

Language: Английский

Citations

5
One-Pot Synthesis of Difluorobicyclo[1.1.1]pentanes from α-Allyldiazoacetates DOI Creative Commons

Jack C. Sharland,

Huw M. L. Davies

Organic Letters, Journal Year: 2023, Volume and Issue: 25(28), P. 5214 - 5219

Published: July 10, 2023

Rapid access to 2,2-difluorobicylco[1.1.1]pentanes is enabled from an α-allyldiazoacetate precursor in a one-pot process through cyclopropanation afford 3-aryl bicyclo[1.1.0]butane, followed by reaction with difluorocarbene the same flask. The modular synthesis of these diazo compounds affords novel 2,2-difluorobicyclo[1.1.1]pentanes that were inaccessible previously reported methods. reactions chiral 2-arylbicyclo[1.1.0]butanes manner generate altogether different products high asymmetric induction, methylene-difluorocyclobutanes. Larger ring systems including bicyclo[3.1.0]hexanes are also rapidly furnished due nature starting material.

Language: Английский

Citations

12