Antiaromatic Compounds; 28. A Synthesis of Pyrrole Derivatives from Tri-tert-butylazete and Isonitriles or Carbon Monoxide

Article abstract of DOI:10.1055/s-1990-27029

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.