Organic reactions catalyzed by 1, 4-diazabicyclo [2.2.2] octane (DABCO)

Abstract

The organic reactions catalyzed by 1, 4-diazabicyclo [2.2.2] octane (DABCO) are reviewed. Most of the reactions start conveniently from available substrate and proceed under mild conditions. The reactions are environmentally friendly and the catalyst can be recycled in some cases. The perspectives on DABCO-catalyzed reactions are pointed out. Keywords 1, 4-diazabicyclo [2.2.2] octane (DABCO), organic synthesis, catalysis 1,4-Diazabicyclo [2.2.2] octane (DABCO, Scheme 1), a cage-like compound, is a small diazabicyclic molecule, which has weak alkalescence, medium-hindrance and widely used in organic synthesis reactions. On the one hand, it can serve as a weak base and ligand, for example, reactions of the Nmethylation of indoles and Pd(OAc) 2 /DABCO-catalyzed Stille cross-coupling reaction, etc. On the other hand, it is also a very widely used catalyst in organic synthesis reactions, for example, the Baylis-Hillman reaction, synthesis of three-membered carbocyclic compounds and heterocyclic reactions containing oxygen, nitrogen. According to the types of products, this paper introduces the application of DABCO in organic synthesis in the recent years.

1,4-Diazabicyclo[2.2.2]octane (DABCO) as a useful catalyst in organic synthesis

“…The reactions are environmentally friendly and the catalyst can be recycled in some cases. DABCO has been reviewed by Yang Hua et al recently [1]. In the following sections, some recent advances in the application of DABCO in organic synthesis will be discussed.…”

An Efficient Synthesis and Antibacterial Activity of Some Novel 2‐Azetidinone Derivatives of 4H‐1,2,4‐Triazoles Under Mild Conditions

“…However, in most of the methods, 2‐azetidinone derivatives have been synthesized from the Schiff bases . By dehydrative cyclo‐addition of Schiff bases using chloroacetyl chloride and Et 3 N as base catalyst; however, some problems in recovering the catalyst, solvents (dioxane), and purification of products have been encountered, so in place of Et 3 N, DABCO (Diaza‐bicyclooctane) catalyst has been the choice of our interest in 2‐azetidinones synthesis due to their low cost and environment‐friendly nature . In continuation with our investigations into the synthesis of novel substituted 1,2,4‐triazoles derivatives with biological activity, and due to several advantages of DABCO catalyst, here we report a new approach for the synthesis of 3‐chloro‐2‐azetidinonyl‐1,2,4‐triazole derivatives using DABCO as a superior basic catalyst.…”

A facile one-pot synthesis of novel 1-substituted 2-(8-hydroxyquinolin-5-yl)-1,5,6,7-tetrahydro-6,6-dimethyl- 4H-indol-4-one derivatives

“…12 In recent years, 1,4-diazabicyclo[2.2.2]octane (DABCO) has emerged as a promoter for various organic reactions. [13][14][15][16][17] DABCO is an organic base that can act as a nucleophile. In view of this, and as part of our work on multi-component reactions, [18][19][20][21][22] we here report a simple, practical, and generally three-component reaction for the synthesis of novel indole derivatives by one-pot three-component reaction of 5-chloroacetyl-8-hydroxyquinoline, alkyl-, aryl-and heteroaryl-amines, and dimedone; the reaction is catalyzed by DABCO.…”