General Synthesis of 3‐Azabicyclo[3.1.1]heptanes and Evaluation of Their Properties as Saturated Isosteres**-Reference-Cited by-同舟云学术

General Synthesis of 3‐Azabicyclo[3.1.1]heptanes and Evaluation of Their Properties as Saturated Isosteres**

Published:2023-06-15 Issue:39 Volume:135 Page:
ISSN:0044-8249
Container-title:Angewandte Chemie
language:en
Short-container-title:Angewandte Chemie

Author:

Dibchak Dmitry¹,Snisarenko Mariya¹,Mishuk Artem¹,Shablykin Oleh¹²,Bortnichuk Lina³,Klymenko‐Ulianov Oleksii³,Kheylik Yurii³,Sadkova Iryna V.¹,Rzepa Henry S.⁴,Mykhailiuk Pavel K.¹^ORCID

Affiliation:

1. Enamine Ltd. Chervonotkatska 60 02094 Kyiv Ukraine

2. Institute of Bioorganic Chemistry and Petrochemistry National Academy of Sciences of Ukraine Akademika Kukharya, 1 02094 Kyiv Ukraine

3. Bienta Chervonotkatska 78 02094 Kyiv Ukraine

4. Department of Chemistry Molecular Sciences Research Hub White City Campus Imperial College London 82 Wood Lane London W12 0BZ UK

Abstract

AbstractA general approach to 3‐azabicyclo[3.1.1]heptanes by reduction of spirocyclic oxetanyl nitriles was developed. The mechanism, scope, and scalability of this transformation were studied. The core was incorporated into the structure of the antihistamine drug Rupatidine instead of the pyridine ring, which led to a dramatic improvement in physicochemical properties.

Funder

HORIZON EUROPE European Research Council

Publisher

Wiley

Subject

General Medicine

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/ange.202304246

Reference70 articles.

1. Synthesis of meta-substituted arene bioisosteres from [3.1.1]propellane

3. Practical and Facile Access to Bicyclo[3.1.1]heptanes: Potent Bioisosteres of meta-Substituted Benzenes

4. Photochemical Intermolecular [3σ + 2σ]-Cycloaddition for the Construction of Aminobicyclo[3.1.1]heptanes

5. Selective [2σ + 2σ] Cycloaddition Enabled by Boronyl Radical Catalysis: Synthesis of Highly Substituted Bicyclo[3.1.1]heptanes

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2. Silver‐Enabled Cycloaddition of Bicyclobutanes with Isocyanides for the Synthesis of Polysubstituted 3‐Azabicyclo[3.1.1]heptanes;Angewandte Chemie;2024-04-15