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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 19
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Original Articles

Dramatically Accelerated Addition Under Solvent-Free Conditions: An Efficient Synthesis of (E)-1,2,4-Triazole-Substituted Alkenes from Baylis–Hillman Acetates

, , , &
Pages 3291-3302 | Received 23 Nov 2007, Published online: 12 Sep 2008
 

Abstract

The addition of 1,2,4-triazole to Baylis–Hillman acetates mediated by Et3N was dramatically accelerated under solvent-free conditions to afford (E)-1,2,4-triazole-substituted alkenes 3 with excellent yields.

ACKNOWLEDGMENTS

We are grateful to the National Natural Science Foundation of China (Nos. 20476098 and 20676123) for financial support.

Notes

a 2.0 mmol of Baylis–Hillman acetates, 2.2 mmol of triazole, and 1.1 mmol of K2CO3 or 2.2 mmol of Et3N were used.

b Isolated yields based on Baylis–Hillman acetates.

c Complex mixture was obtained.

d The starting material was recovered.

e The ratio of 3a and 4a was determined from the 1H NMR spectrum.

a 2.0 mmol of Baylis–Hillman acetates, 2.2 mmol of triazole, and 2.2 mmol of Et3N were used.

b Isolated yields based on Baylis–Hillman acetates.

c The addition was very slow in the absence of Et3N.

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