107554-57-4Relevant academic research and scientific papers
The synthesis of pyrroles and dihydropyrroles by 1,3-dipolar cyclisations of N-arylmethylene[(benzotriazol-1-yl)arylmethyl]amines
Katritzky,Hitchings,Zhao
, p. 863 - 867 (2007/10/02)
N-Arylmethylene[(benzotriazol-1-yl)arylmethyl]amines 1 are prepared by the reaction of arylaldehydes, benzotriazole, and ammonia in dry ethanol. Deprotonation of these imines with butyllithium yields N-lithiated azomethine ylides 2 which readily undergo 1,3-dipolar cycloaddition with a large range of dipolarophiles. The cyclisations are regiospecific and generally exhibit high stereoselectivity. Benzotriazolate is eliminated during the course of the reaction, and the method thereby provides a route to 2,5-diaryl substituted pyrroles, 3,4-dihydro-2H-pyrroles and c-ring fused 3,4-dihydro-2H-pyrroles.
Stereoselectivity of Cycloaddition of N-(Cyanomethyl)- and N-(α-Cyanobenzyl)imines with Olefinic Dipolarophiles. Synthetic Equivalents of Nitrile Ylide 1,3-Dipoles
Tsuge, Otohiko,Ueno, Kazunori,Kanemasa, Shuji,Yorozu, Kiyotaka
, p. 1809 - 1824 (2007/10/02)
N-(Cyanomethyl)- and N-(α-cyanobenzyl)imines derived from a variety of aldehydes and ketones can tautomerize into N-protonated azomethine ylides which undergo cycloadditions with olefinic dipolarophiles.These cycloadditions are often accompanied by the el
