A convenient four-component one-pot strategy toward the synthesis of pyrazolo[3,4-d]pyrimidines

Mingxing Liu; Jiarong Li; Hongxin Chai; Kai Zhang; Deli Yang; Qi Zhang; Daxin Shi

doi:10.3762/bjoc.11.229

A convenient four-component one-pot strategy toward the synthesis of pyrazolo[3,4-d]pyrimidines

Beilstein J Org Chem. 2015 Nov 6:11:2125-31. doi: 10.3762/bjoc.11.229. eCollection 2015.

Authors

Mingxing Liu¹, Jiarong Li¹, Hongxin Chai¹, Kai Zhang¹, Deli Yang¹, Qi Zhang¹, Daxin Shi¹

Affiliation

¹ School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing, 100081, China.

Abstract

An efficient one-pot synthesis of pyrazolo[3,4-d]pyrimidine derivatives by the four-component condensation of hydrazines, methylenemalononitriles, aldehydes and alcohols has been developed via two different reaction pathways. The structures of target products were characterized by IR spectroscopy, NMR ((1)H and (13)C) spectroscopy and HRMS (ESI) spectrometry. The crystal structure of 4-ethoxy-6-(2-nitrophenyl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine was determined by single crystal X-ray diffraction.

Keywords: four-component; one-pot; pyrazolo[3,4-d]pyrimidine; sodium alkoxide.