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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 5
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Original Articles

Practical and General Entry to N‐Tosyl Aryl Aldimines Promoted by Sulfamic Acid in Water and Alcohol

Zhenjiang Li College of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Nanjing, ChinaCorrespondence[email protected]
,
Xinhua Ren College of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Nanjing, China
,
Yuhu Shi College of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Nanjing, China
&
Pingkai Ouyang College of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Nanjing, China
Pages 713-724 | Published online: 10 Mar 2007
 
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Abstract

A practical, indirect procedure composed of a three‐component condensation using aromatic aldehydes, p‐tosylamide, and sodium p‐toluenesulfinate in the presence of sulfamic acid in tap water–alcohol solvents to afford amidosulfones, and the subsequent water two‐phase basic elimination of the amidosulfones to N‐tosyl arylimines, was developed. The process has little environmental impact, easy workup, mild reaction conditions, and good yields and is amenable to large‐scale preparations.

Acknowledgment

This work was supported by the Major Basic Research and Development Program of China (Grant No. 2003CB716004).

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