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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 14
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Original Articles

Combining a Click–Multicomponent Reaction: One-Pot Synthesis of 1,2,3-Triazol-4-ylmethyl 3-Amino-5,10-dihydro-5,10-dioxo-1H-pyrazolo[1,2-b]phthalazine-2-carboxylate Derivatives

, , , , &
Pages 2037-2044 | Received 15 Oct 2013, Published online: 09 Jun 2014
 

Abstract

(1,2,3-Triazol-4-yl)methyl-3-amino-5,10-dihydro-5,10-dioxo-1H-pyrazolo[1,2-b]phthalazine-2-carboxylate derivatives were synthesized by a four-component, one-pot condensation reaction of benzaldehyde derivatives, an active methylene compound (prop-2-ynyl-2-cyanoacetate), azides, and phthalhydrazide in the presence of Cu(OAc)2/sodium ascorbate as catalysts and 1-methyl-1H-imidazolium trifluoroacetate ([Hmim]TFA) as an ionic liquid medium in good to excellent yields.

GRAPHICAL ABSTRACT

Notes

a Reaction conditions: 4-chlorobenzaldehyde 1a (0.14 g, 1 mmol), 1-azido-3-nitrobenzene 2a (0.16 g, 1 mmol), prop-2-ynyl 2-cyanoacetate 3 (0.14 g, 1.2 mmol), phthalhydrazide 4 (0.16 g, 1 mmol), Cu(OAC)2 (0.02 g, 10 mol%), sodium ascorbate (0.04 g, 20 mol%), solvent (10 mL), 4 h.

b Cu(OAC)2 (0.02 g, 10 mol%), sodium ascorbate (0.04 g, 20 mol%), and p-TSA (0.34 g, 20 mol%).

c Cu(OAC)2 (0.02 g, 10 mol%), sodium ascorbate (0.04 g, 20 mol%), and [Hmim]TFA (10 mol%).

d CuI (0.019 g, 10 mol%) and [Hmim]TFA (10 mol%).

e CuSO4 (0.016 g, 10 mol%), sodium ascorbate (0.04 g, 20 mol%), and [Hmim]TFA (10 mol%).

f CuCl2 (0.013 g, 10 mol%), sodium ascorbate (0.04 g, 20 mol%), and [Hmim]TFA (10 mol%).

g Cu(OAC)2 (0.01 g, 5 mol%), sodium ascorbate (0.02 g, 10 mol%), and [Hmim]TFA (10 mol%).

Color versions of one or more of the figures in the article can be found online at www.tandfonline.com/lsyc.

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