91406-83-6Relevant academic research and scientific papers
Preparation of Secondary Amines and β-Amino esters via Additions of Grignard and Reformatsky Reagents to Imines and by One-Pot Reactions of Primary Amines, Aldehydes, and Grignards
Katritzky, Alan R.,Hong, Quingmei,Yang, Zhijun
, p. 3405 - 3408 (2007/10/02)
Additions of Grignard and Reformatsky reagents to imines in the presence of 1-(trimethylsilyl)benzotriazole afforded in good yields the corresponding secondary amines and β-amino esters.The procedure is general as imines containing hydrogens α to both carbon and nitrogen can be employed.Extensions of this method to include imines containing other Lewis basic centers, e.g., those derived from furan-, thiophene-, indole-, and p-methoxybenzenecarboxaldehyde, have been successful in avoiding the potential complications which could result from the use of a Lewis acid as the activating species.The imines need not be isolated, and a one-pot method for the synthesis of secondary amines from aldehydes, primary amines, and Grignard reagents is described.
A convergent one-pot synthesis of secondary amines via aza-Wittig reaction
Gajda,Koziara,Osowska-Pacewicka,Zawadzki,Zwierzak
, p. 1929 - 1938 (2007/10/02)
Secondary amines are obtained in moderate-good yields by reduction of crude imines prepared from N-alkyltriethoxyiminophosphoranes and aldehydes via the aza-Wittig reaction. N-Alkyltriethoxyiminophosphoranes are synthesized by one-pot azidation of alkyl bromides followed by Staudinger reaction.
Rate constants for aryl radical cyclization of aldimines: Synthesis of tetrahydroisoquinolines by fast 6-endo closures to carbon
Tomaszewski,Warkentin
, p. 2123 - 2126 (2007/10/02)
Aryl radicals cyclize to an imino functional group in a competition involving 6-endo closure to C and 5-exo closure to N. there is a large 6-endo preference forming tetrahydroisoquinolinyl radicals with k(6-endo) (80°C) > 108 s-1.
