Organocatalytic hetero [4+2] cycloaddition reactions of 2-(1-alkynyl)-2-alkene-1-ones: metal-free access to highly substituted 4H-pyrans.

نویسندگان

  • Xiuzhao Yu
  • Zhongyan Cao
  • Junliang Zhang
چکیده

Highly substituted 4H-pyrans can be smoothly synthesized from readily available 2-(1-alkynyl)-2-alkene-1-ones by DBU- or n-Bu(3)P catalyzed hetero-[4+2] cycloaddition reactions, in which 2-(1-alkynyl)-2-alkene-1-ones act as both heterodiene and heterodinenophile.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

The Chemistry of Heteroarylphosphorus Compounds, Part 14 [1] Effects of Heteroaryl Substituents at Phosphorus on the Steric Course of Wittig Reactions of Semistabilised and Stabilised Ylides

Alkene cis-trans Ratio, Betaine Mechanism, Cycloaddition Mechanism The cis-trans ratio of the stilbenes formed in Wittig reactions of semistabilised ylides (derived from benzyltri(hetero)arylphosphonium salts in ethanolic ethoxide) with benzaldehyde decreases markedly in the series 2-furyl >2-thienyl >phenyl > 1-methylpyrrol2-yl. The 2-furyl group favours a greater proportion of the ci«-isomer ...

متن کامل

A Simple Access to the Synthesis of 5,6- Dihydro-4H-1,3-oxazines Under Solvent Free Condition and Microwave Irradiation

2-Arylsubstituted 5,6-dihydro-4H-1,3-oxazines were conveniently synthesized by the condensation of 3-aminopropanol and desired carboxylic acids under solvent free and microwave conditions in short reaction times with moderate to good yields. A comparison of this method with the classical protocols using acid halides and nitrile substrates was also made. INTRODUCTION The synthetic utility of dih...

متن کامل

Synthesis of some new substituted azetidinonyl and thiazolidinonyl quinazolon-4(3H)-ones as potential non-steroidal anti-inflammatory and analgesic agents

A series of 2-(5-(6-Bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-4H-1,2,4-triazole-3-ylthio)-N-(substituted benzylidene) acetohydrazides (5a-5l) have been synthesized via condensation of 2-(5-(6-Bromo-2-methyl-4-oxaquinazolin-3 (4H)-yl)-4H-1,2,4-triazole-3-ylthio)acetohydrazide (4) with different aromatic aldehydes. Cycloaddition of thioglycolic acid with 5a-5l yielded 2-[5-(6-Bromo-2-methyl-4-oxoq...

متن کامل

Formal [2 + 2 + 2] cycloaddition strategy based on an intramolecular propargylic ene reaction/Diels-Alder cycloaddition cascade.

A formal, metal-free, [2 + 2 + 2] cycloaddition strategy is described based on a cascade of two pericyclic processes. The first step involves an intramolecular propargylic ene reaction of a 1,6-diyne to generate a vinylallene, which then reacts in an inter- or intramolecular Diels-Alder reaction with an alkenyl or alkynyl dienophile. Reactions involving unsymmetrical alkenyl and alkynyl dienoph...

متن کامل

Recent Advances in Inverse-Electron-Demand Hetero-Diels–Alder Reactions of 1-Oxa-1,3-Butadienes

This review is an endeavor to highlight the progress in the inverse-electron-demand hetero-Diels-Alder reactions of 1-oxa-1,3-butadienes in recent years. The huge number of examples of 1-oxadienes cycloadditions found in the literature clearly demonstrates the incessant importance of this transformation in pyran ring synthesis. This type of reaction is today one of the most important methods fo...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Organic & biomolecular chemistry

دوره 8 22  شماره 

صفحات  -

تاریخ انتشار 2010