Conversion of Medium-Sized Lactams to α-Vinyl or α-Acetylenyl Azacycles via N,O-Acetal TMS Ethers-Reference-Cited by-同舟云学术

Conversion of Medium-Sized Lactams to α-Vinyl or α-Acetylenyl Azacycles via N,O-Acetal TMS Ethers

Published:2018-11-19 Issue:11 Volume:23 Page:3023
ISSN:1420-3049
Container-title:Molecules
language:en
Short-container-title:Molecules

Author:

Kim Minjun,Jang Jaebong,Choi Goyoung,Chung Sungkyun,Lim Changjin,Hur Joonseong,Kim Hyun,Na Younghwa,Son Woo,Suh Young-Ger,Jung Jong-Wha,Kim Seok-Ho^ORCID

Abstract

α-Vinyl or α-acetylenyl azacycles were easily synthesized from 7- to 9-membered lactams and 6- to 9-membered lactams via N,O-acetal trimethylsilyl (TMS) ethers. Organocopper and organostannane reagents afforded reasonable yields for the respective N-acyliminium ion vinylation and acetylenylation intermediates generated from N,O-acetal TMS ethers in the presence of a Lewis acid.

Funder

National Research Foundation of Korea

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

Link

http://www.mdpi.com/1420-3049/23/11/3023/pdf

Reference21 articles.

1. Scaffold Diversity from N-Acyliminium Ions

2. Biological and conformational study of β-substituted prolines in MT-II template: steric effects leading to human MC5 receptor selectivity*

3. Alkynylation of thiolactams. New synthesis of α-substituted pyrrolidine and piperidine alkaloids

4. Construction of Hydroxylated Alkaloids (.+-.)-Mannonolactam, (.+-.)-Deoxymannojirimycin, and (.+-.)-Prosopinine through Aza-Annulation

5. Total Synthesis of the Marine Alkaloid (±)-Lepadiformine via a Radical Carboazidation

Cited by 6 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. Gold(I)‐Catalyzed Alkynylation of N,O‐Acetals: An Access to Alkynylated Saturated N‐heterocycles;Advanced Synthesis & Catalysis;2023-02-07

2. Azepines and Their Fused-Ring Derivatives;Comprehensive Heterocyclic Chemistry IV;2022

3. Hydantoin-bridged medium ring scaffolds by migratory insertion of urea-tethered nitrile anions into aromatic C–N bonds;Chemical Science;2021

4. Unexpected Rearrangement of N-Allyl-2-phenyl-4,5-Dihydrooxazole-4-Carboxamides to Construct Aza-Quaternary Carbon Centers;Molecules;2019-12-08

5. Aptamer-functionalized liposomes for targeted cancer therapy;Cancer Letters;2019-04