Preparation of 4-anilino-6-aryl-2H-pyran-2-ones from trilithiated acetoacetanilides and aromatic esters-Reference-Cited by-同舟云学术

Preparation of 4-anilino-6-aryl-2H-pyran-2-ones from trilithiated acetoacetanilides and aromatic esters

Published:2004-05-01 Issue:5 Volume:82 Page:659-664
ISSN:0008-4042
Container-title:Canadian Journal of Chemistry
language:en
Short-container-title:Can. J. Chem.

Author:

Downs Jennifer R,Grant Sally P,Townsend Jessica D,Schady Deborah A,Pastine Stefan J,Embree Mildred C,Metz Clyde R,Pennington William T,Bailey Walsch Rosa D,Beam Charles F

Abstract

Acetoacetanilide and 4′-chloroacetoacetanilide were trilithiated with excess lithium diisopropylamide and condensed with several aromatic esters, followed by neutralization, separate acid cyclization, and rearrangements. After C-acylation of trilithiated acetoacetanilides and cyclization to 4H-pyran-4-ones, these compounds underwent multistep rearrangements to 4-anilino-6-aryl-2H-pyran-2-ones.Key words: pyranones, trianions, Claisen-type condensations, rearrangements.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

Link

http://www.nrcresearchpress.com/doi/pdf/10.1139/v04-029

Reference11 articles.

1. Condensations at the Methyl Group of Ethyl Acetoacetate by Means of Potassium Amide or Sodium Hydride1

2. Condensations at the Methyl Group Rather than the Methylene Group of Benzoyl-and Acetylacetone Through Intermediate Dipotassio Salts1

3. The Preparation of 2-(4-Oxo-4H-1-benzopyran-2-yl)-1-phenyl-ethanones by the Condensation/Cyclization of Dilithiated 1-Benzoylacetone with Lithiated Methyl Salicylates

4. Heterocyclic photochemistry. 2. 4-Pyrones. A mechanistic study

Cited by 9 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. Experimental and Theoretical Investigation of the Structure of Acetoacetanilide;Russian Journal of General Chemistry;2022-11

2. Synthesis and Crystal Structure Determination of 3-Phenyl-2-(2-phenylhydrazino)-4H-1-benzothiopyran-4-one;Journal of Chemical Crystallography;2010-01-30

3. Preparation ofNH-pyrazoleacetic acid anilides from trilithiated acetoacetanilide, select aromatic esters, and hydrazine;Journal of Heterocyclic Chemistry;2010

4. Cycloaddition reactions of cross-conjugated enaminones;Tetrahedron;2009-10

5. New Strong Base Synthesis of Symmetrical 1,5-Diaryl-1,3,5-pentanetriones from Acetone and Benzoate Esters;Synthetic Communications;2008-06-27