One-Pot Tandem 1,3-Dipolar Cycloaddition of Azinium Ylides Using Water as Solvent

Title:One-Pot Tandem 1,3-Dipolar Cycloaddition of Azinium Ylides Using Water as Solvent

Volume: 1 Issue: 3

Author(s): Deepika Singh, Pragya Sinha and Raj K. Bansal

Affiliation:

Keywords: Azinium ylides, 1, 3-Dipolar cycloaddition, DMAD, maleic anhydride, pyrrolo[1, 2-f]phenanthridines, water as solvent.

Abstract: Following an important principle of Green Chemistry, namely the use of a benign solvent, the reaction of azines, namely pyridine, isoquinoline and phenanthridine with phenacyl bromides or with t-butyl bromoacetate has been accomplished in water to generate an aqueous solution of the (substituted methyl)azinium bromides, which on further reacting with dimethyl acetylenedicarboxylate (DMAD) and potassium carbonate furnish annelated pyrroles through tandem formation of the azinium methylides followed by 1,3-dipolar cycloaddition. In one case, maleic anhydride could also be used as 1,3-dipolarophile. The products are obtained in good yields and have been well characterized.

Cite this article as:

Singh Deepika, Sinha Pragya and Bansal K. Raj, One-Pot Tandem 1,3-Dipolar Cycloaddition of Azinium Ylides Using Water as Solvent, Current Green Chemistry 2014; 1 (3) . https://dx.doi.org/10.2174/2213346101666140210194354