O-Cyclopropyl hydroxylamines: gram-scale synthesis and utility as precursors for N-heterocycles-Reference-Cited by-同舟云学术

O-Cyclopropyl hydroxylamines: gram-scale synthesis and utility as precursors for N-heterocycles

Published:2020 Issue:17 Volume:18 Page:3281-3287
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Lovato Kaitlyn¹²³⁴^ORCID,Bhakta Urmibhusan¹²³⁴,Ng Yi Pin⁵⁶⁷⁸,Kürti László¹²³⁴^ORCID

Affiliation:

1. Department of Chemistry

2. Rice University

3. Bioscience Research Collaborative Houston

4. USA

5. Division of Chemistry and Biological Chemistry

6. School of Physical & Mathematical Sciences

7. Nanyang Technological University

8. Singapore

Abstract

A novel and scalable synthesis of O-cyclopropyl hydroxylamines is reported. These compounds are bench-stable and have been shown to be practical precursors for the synthesis of N-heterocycles via a di-heteroatom [3,3]-sigmatropic rearrangement.

Funder

National Institute of General Medical Sciences

Division of Chemistry

Welch Foundation

Division of Graduate Education

Nanyang Technological University

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2020/OB/D0OB00611D

Reference30 articles.

1. Molecular rearrangements in organic synthesis , ed. C. M. Rojas , John Wiley & Sons, Inc. , Hoboken, New Jersey , 2015 , pp. 522–537

2. The reaction of vinyl grignard reagents with 2-substituted nitroarenes: A new approach to the synthesis of 7-substituted indoles

3. T. L. Cottrell , The Strengths of Chemical Bonds , 2nd edn, Butterworths , London , 1958

4. Bonding Properties of Cyclopropane and Their Chemical Consequences

5. Modern Developments in the Chemistry of Homoenolates

Cited by 12 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. Selective silver (I)-catalyzed four-component gram-scale synthesis of novel 1,4-disubstituted 1,2,3-triazole-sulfonamides under heterogeneous catalysis and microwave irradiation in water;Results in Chemistry;2022-01

2. [3,3]-Sigmatropic rearrangements: a variety of methods and recent advances;Russian Chemical Reviews;2022

3. Selective Silver (I)-Catalyzed Four-Component Gram-Scale Synthesis of Novel 1,4-Disubstituted 1,2,3-Triazole-Sulfonamides Under Heterogeneous Catalysis and Microwave Irradiation in Water;SSRN Electronic Journal;2022

4. Diaryliodonium Salt-Based Synthesis of N-Alkoxyindolines and Further Insights into the Ishikawa Indole Synthesis;The Journal of Organic Chemistry;2021-07-01

5. Sc(OTf)3-catalyzed [3 + 2]-cycloaddition of nitrones with ynones;Organic & Biomolecular Chemistry;2021