Department of Chemistry , University of Illinois at Chicago , 845 West Taylor Street , Chicago , Illinois 60607-7061 , United States.
J Org Chem. 2019 Oct 4;84(19):12430-12436. doi: 10.1021/acs.joc.9b01885. Epub 2019 Sep 17.
An efficient, one-pot method for the preparation of 5-(1-hydroxyalkyl)tetrazoles is reported. Morpholinomethyl-5-lithiotetrazole, generated by the deprotonation of 4-(-tetrazolylmethyl)morpholine with LiHMDS, undergoes addition to ketones and aldehydes (both aromatic and aliphatic) to form 5-(1-hydroxyalkyl)tetrazoles in a high yield, after acidic workup. The reported protocol displays a broad substrate scope and functional group tolerance, avoids the use of cyanide- or azide-based reagents, and provides access to sterically congested and unsaturated tetrazoles, which are difficult to access by other means.
本文报道了一种高效、一锅法制备 5-(1-羟烷基)四唑的方法。通过 LiHMDS 脱质子生成的吗啉甲基-5-锂代四唑与酮和醛（芳基和脂肪族）加成，经酸性后处理得到高产率的 5-(1-羟烷基)四唑。该方法具有广泛的底物范围和官能团容忍性，避免了使用氰化物或叠氮化物试剂，并提供了获得空间位阻大和不饱和四唑的途径，这些四唑很难通过其他方法获得。
