Convenient Preparations of Imines and Symmetrical Secondary Amines Possessing Primary or Secondary Alkyl Groups
作者:Alan R. Katritzky、Xiaohong Zhao、Gregory J. Hitchings
DOI:10.1055/s-1991-26551
日期:——
Hindered alkyl aldehydes react with benzotriazole and ammonia in dry ethanol or methanol to yield the corresponding bis[1-(benzotriazol-1-yl)alkyl]amines 2. The reaction of aryl aldehydes, however, yields 1-(benzotriazol-1-yl)-N-alkylidenealkylamines 3. The reactions of adducts 2 and 3 with lithium aluminum hydride furnishes dialkyl- and dibenzylamine derivatives 4. Although the reactions of 2 and 3 with organometallic reagents are not as general, in several cases the reactions of amines 2 with Grignard reagents yield 1-alkyl or aryl substituted N-alkylidenealkylamines 5. Similar reactions of amines 2 with phenyl lithium afford 1,1′-diphenyldialkylamines 7.
受阻的烷基醛与苯并三唑和氨在无水乙醇或甲醇中反应,生成相应的双[1-(苯并三唑-1-基)烷基]胺2。而苯基醛的反应则生成1-(苯并三唑-1-基)-N-亚烷基烷基胺3。这些加合物2和3与氢化锂铝反应,得到二烷基胺和二苄基胺衍生物4。尽管2和3与有机金属试剂的反应不像那么普遍,但在某些情况下,胺2与格氏试剂反应生成1-烷基或苯基取代的N-亚烷基烷基胺5。类似的,胺2与苯基锂反应生成1,1′-二苯基二烷基胺7。