Synthesis p. 834 - 840 (1990)
Update date:2022-07-29
Topics:
Hees, Udo
Schneider, Juergen
Wagner, Oliver
Regitz, Manfred
The kinetically stabilized azete 4 reacts with isonitriles 5 in a sequence of <4+1> cycloaddition and ring-opening steps to yield 2- and 3-imino substituted 2H- and 3H-pyrrole derivatives 8, 9.The α-methylene isonitriles 10 react analogously, but the formation of 2- and 3-iminopyrroles is still followed by an <1,5>-shift which leads to 2- and 3-aminopyrroles 13, 14.With carbon monoxide the azete 4 is transformed into the 2H-pyrrole-2-one and 3H-pyrrole-3-one 18 and 19.
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Doi:10.1016/j.tetlet.2011.02.093
(2011)Doi:10.1016/S0040-4039(00)97246-0
(1990)Doi:10.1021/jo00011a050
(1991)Doi:10.1021/jo0260084
(2003)Doi:10.1016/S0040-4020(02)00680-4
(2002)Doi:10.1002/1099-0690(200301)2003:1<209::AID-EJOC209>3.0.CO;2-S
(2003)