Efficient Solvent-free Synthesis of Spiro Heterobicyclic Derivatives with Boric Acid as Catalyst

doi:10.11944/j.issn.1000-0518.2015.09.150038

Chinese Journal of Applied Chemistry ›› 2015, Vol. 32 ›› Issue (9): 999-1004.DOI: 10.11944/j.issn.1000-0518.2015.09.150038

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Efficient Solvent-free Synthesis of Spiro Heterobicyclic Derivatives with Boric Acid as Catalyst

XU Zhaohui(),LIU Deyong,TU Yuanhong

National Monosaccharide Chemical Synthesis Engineering Research Center, Jiangxi Normal University,Nanchang 330027,China

Received:2015-02-02 Accepted:2015-05-08 Published:2015-08-31 Online:2015-08-31
Contact: XU Zhaohui
Supported by:
Supported by the National Science and Technology Project(No.2001BA323C), the Graduate Innovation Foundation of Jiangxi Province(No.YC2015-B030)

Abstract

Abstract:

Eight spiro heterobicyclic compounds were synthesized by the three component condensation reaction of aromatic aldehydes with urea and 2,2-dimethyl-1,3-dioxane-4,6-dione using boric acid as catalyst under solvent-free conditions. The results indicate that the yields range from 84% to 94% at 80 ℃ for 2.0~4.0 h using 10% molar fraction of boric acid(relative to the substrate of 2,2-dimethyl-1,3-dioxane-4,6-dione). Furthermore, a mechanism for the reaction catalyzed by boric acid was proposed. The main advantages of the present procedure are mild conditions, short reaction time and high yields.

Key words: boric acid, solvent-free, three component condensation reaction, spiro heterobicyclic derivatives

XU Zhaohui,LIU Deyong,TU Yuanhong. Efficient Solvent-free Synthesis of Spiro Heterobicyclic Derivatives with Boric Acid as Catalyst[J]. Chinese Journal of Applied Chemistry, 2015, 32(9): 999-1004.

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Efficient Solvent-free Synthesis of Spiro Heterobicyclic Derivatives with Boric Acid as Catalyst

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