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Nhazırlanması-(2-alkoxyvinyl) N- tosyl-1,2,3-triazoles ve yerine Phthalans ve f...
Nhazırlanması-(2-alkoxyvinyl) N- tosyl-1,2,3-triazoles ve yerine Phthalans ve f...
JoVE Journal
Chemistry
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JoVE Journal Chemistry
Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Nhazırlanması-(2-alkoxyvinyl) N- tosyl-1,2,3-triazoles ve yerine Phthalans ve fenitilaminler sonraki dönüşüm sülfonamidler

Full Text
10,348 Views
10:42 min
January 3, 2018

DOI: 10.3791/56848-v

John M. Bennett1, Jonathan D. Shapiro1, Krystina N. Choinski1, Yingbin Mei1, Sky M. Aulita1, Giovanny M. Dominguez1, Max M. Majireck1

1Chemistry Department,Hamilton College

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Overview

This report presents an efficient methodology for synthesizing N-(2-alkoxyvinyl)sulfonamides and converting them into valuable heterocycles like phthalans and phenethylamines. The techniques demonstrated are particularly useful for handling unstable synthetic intermediates.

Key Study Components

Area of Science

  • Synthetic Chemistry
  • Organic Synthesis
  • Heterocyclic Chemistry

Background

  • N-(2-alkoxyvinyl)sulfonamides are versatile functional groups.
  • They can be converted into various valuable compounds.
  • Handling unstable intermediates is a common challenge in organic synthesis.
  • This study aims to address these challenges with a new methodology.

Purpose of Study

  • To demonstrate a method for synthesizing N-(2-alkoxyvinyl)sulfonamides.
  • To illustrate reactions that convert these sulfonamides into heterocycles.
  • To provide techniques for managing unstable synthetic intermediates.

Methods Used

  • Preparation of N-(2-alkoxyvinyl)sulfonamides.
  • Conversion of sulfonamides to phthalans and phenethylamines.
  • Use of copper-thiophene-carboxylate in the synthesis process.
  • Application of microwave-assisted techniques for efficiency.

Main Results

  • Successful synthesis of N-(2-alkoxyvinyl)sulfonamides.
  • Effective conversion to valuable heterocycles demonstrated.
  • Methodology allows for handling of acid-sensitive compounds.
  • Demonstration by an undergraduate student highlights educational aspects.

Conclusions

  • The methodology provides a reliable approach to synthesizing complex organic compounds.
  • It enhances the synthetic potential of nitrogen and oxygen-containing synthons.
  • Future research can build on these techniques for further applications.

Frequently Asked Questions

What are N-(2-alkoxyvinyl)sulfonamides?
They are versatile functional groups used in organic synthesis.
How are these compounds synthesized?
Through a detailed methodology involving specific reagents and conditions.
What is the significance of this research?
It provides new methods for synthesizing valuable heterocycles.
Who conducted the demonstration?
Giovanny Dominguez, an undergraduate student from the laboratory.
What challenges does this methodology address?
It helps manage unstable synthetic intermediates effectively.
What are the potential applications of this research?
It can be used to explore new synthetic pathways in organic chemistry.

Nsentezi için temsil edici deneysel prosedürler-(2-alkoxyvinyl) sülfonamidler ve sonraki phthalan ve fenetilamin türevleri için ayrıntılı olarak sunulmaktadır.

Bu raporun genel amacı, sentetik olarak çok yönlü bir fonksiyonel grup olan N-2-alkoksi vinil sülfonamidlere erişim için etkili bir metodoloji göstermek ve bu grubu ftalanlar ve fenetilaminler gibi değerli heterosikllere dönüştüren çeşitli reaksiyonları göstermektir. Bu yöntem, aside duyarlı organik bileşikler gibi kararsız sentetik ara ürünlerin işlenmesi için bazı genel teknikleri göstermektedir. Tekniğimizin ana özelliği, kimyagerlerin bu değerli nitrojen ve oksijen içeren senkronun sentetik potansiyelini keşfetmelerini sağlayan N-2-alkoksi vinil sülfonamidlerin verimli bir şekilde üretilmesidir.

Bu prosedürü göstermek, laboratuvarımdan bir lisans öğrencisi olan Giovanny Dominguez olacak. İlk olarak, manyetik bir karıştırma çubuğu içeren fırında kurutulmuş bir mikrodalga şişesine 139 miligram 2-etinilbenzil alkol ve 20 miligram bakır-tiyofen-karboksilat ekleyin. Şişeyi bir septum kapağı ve kıvırıcı ile güvenli bir şekilde kapatın.

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