Synthesis of novel 5-alkyl/aryl/heteroaryl substituted diethyl 3,4-dihydro-2H-pyrrole-4,4-dicarboxylates by aziridine ring expansion of 2-[(aziridin-1-yl)-1-alkyl/aryl/heteroaryl-methylene]malonic acid diethyl esters

• Satish S. More,
• T. Krishna Mohan,
• Y. Sateesh Kumar,
• U. K. Syam Kumar and
• Navin B. Patel

Beilstein J. Org. Chem. 2011, 7, 831–838, doi:10.3762/bjoc.7.95

• chemistry and new applications of these compounds are being continuously explored [10][11][12][13][14][15][16][17][18][19][20][21][22]. However, not much attention has been paid to N-vinyl substituted aziridines. Thus, N-vinyl substituted aziridines provide an opportunity for researchers to explore their

• use for the development of novel synthetic methodologies and for various organic transformations. Recently, the ring opening of N-vinyl substituted aziridines by selenide nucleophiles to furnish functionalized open chain compounds has been described [23]. N-vinyl substituted aziridines can be

• converted into pyrrolines by ring expansion using various dipolarophiles [24][25] as well as by thermal ring expansion [26][27]. The literature also suggests that N-vinyl substituted aziridines can undergo iodide ion mediated ring expansion reactions to yield pyrroline derivatives [13][14]. However, iodide