On the scope of oxidation of tertiary amines: Meisenheimer rearrangements versus Cope elimination in 2-(cyanoethyl)-2-azanorbornanes-Reference-Cited by-同舟云学术

On the scope of oxidation of tertiary amines: Meisenheimer rearrangements versus Cope elimination in 2-(cyanoethyl)-2-azanorbornanes

Published:2016 Issue:12 Volume:3 Page:1624-1634
ISSN:2052-4129
Container-title:Organic Chemistry Frontiers
language:en
Short-container-title:Org. Chem. Front.

Author:

Sousa Carlos A. D.¹²³⁴^ORCID,Sampaio-Dias Ivo E.⁵²³⁴,García-Mera Xerardo⁶⁷⁸⁹,Lima Carlos F. R. A. C.¹⁰¹¹¹²⁴¹³^ORCID,Rodríguez-Borges José E.⁵²³⁴

Affiliation:

1. REQUIMTE/LAQV

2. Departamento de Química e Bioquímica da Universidade do Porto

3. 4169-007 Porto

4. Portugal

5. REQUIMTE/UCIBIO

6. Departamento de Química Orgánica

7. Facultade de Farmacia

8. Universidade de Santiago de Compostela

9. Spain

10. CIQ-UP

11. Departamento de Química e Bioquímica

12. Faculdade de Ciências da Universidade do Porto

13. Departamento de Química & QOPNA

Abstract

When oxidized, exo-2-(cyanoethyl)-2-azanorbornene is prone to [1,2]-Meisenheimer rearrangement, its endo isomer undergoes [2,3]-Meisenheimer and exo/endo-2-(cyanoethyl)-2-azanorbornanes afford N-hydroxylamines through Cope elimination.

Funder

Fundação para a Ciência e a Tecnologia

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2016/QO/C6QO00330C

Reference49 articles.

1. M. B. Smith and J.March, March's Advanced Organic Chemistry, Wiley-Interscience, 6th edn, 2007

2. J. J. Li , Name Reactions - A Collection of Detailed Mechanisms and Synthetic Applications, Springer, Heidelberg, 4 edn, 2009

3. L. Kürti and B.Czakó, Strategic Applications of Named Reactions in Organic Synthesis, Elsevier Academic Press, USA, 2005

4. Structural analysis of three methyl N-phosphorylated 5,6-dihydroxy-2-azabicyclo[2.2.1]heptane-3-carboxylates

5. The first example of the Fischer–Hepp type rearrangement in pyrimidines

Cited by 8 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Synthesis of High-Order and High-Oxidation State Securinega Alkaloids;Accounts of Chemical Research;2023-01-03

2. N-Hydroxy pipecolic acid methyl ester is involved in Arabidopsis immunity;Journal of Experimental Botany;2022-10-19

3. Collective total synthesis of C4-oxygenated securinine-type alkaloids via stereocontrolled diversifications on the piperidine core;Nature Communications;2022-09-02

4. 1,2-Oxazines and Their Benzo Derivatives;Comprehensive Heterocyclic Chemistry IV;2022

5. A Convenient On-Site Oxidation Strategy for the N-Hydroxylation of Melanostatin Neuropeptide Using Cope Elimination;Synthesis;2021-11-11