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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 22
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Original Articles

Highly Chemoselective Condensation of β-Naphthol, Aldehyde, and Urea Catalyzed by Thiamine Hydrochloride

, &
Pages 3424-3432 | Received 08 Apr 2010, Published online: 26 Jul 2011
 

Abstract

A three-component condensation reaction involving β-naphthol, aldehyde, and urea in the presence of 10 mol% thiamine hydrochloride (VB1) as a catalyst is described. Aromatic aldehydes bearing different functional groups exhibited different behavior than β-naphthol and urea under similar reaction conditions. A possible mechanism to account for the reaction is proposed.

ACKNOWLEDGMENTS

This work was supported by the Chinese National Science and Technology Major Project “Key New Drug Creation and Manufacturing Program” (Grants 2009ZX09301-001 and 2009ZX09102), the Chinese National High-Tech Research and Developed Program (Grant 2007AA02Z147), the National Natural Science Foundation of China (Grants 90713046, 30772638, and 30925040), and the CAS Foundation (Grant KSCX2-YW-R-179).

Notes

a Conditions: β-naphthol 1a (5 mmol), aldehyde 2 (5 mmol), urea 3 (7.5 mmol), VB1 (0.5 mmol), 150 °C for 30 min.

b Isolated yield.

a Conditions: β-naphthol 1 (5 mmol), aldehyde 2b or 2f (5 mmol), and urea 3 (7.5 mmol).

b Isolated yields.

a Conditions: β-naphthol 1a (10 mmol), aldehyde 2 (5 mmol), VB1 (0.5 mmol), 150 °C for 30 min.

b Isolated yields.

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