Novel cycloaddition of nitriles with monolithio- and dilithiobutadienes

Jinglong Chen; Qiuling Song; Congyang Wang; Zhenfeng Xi

doi:10.1021/ja0262176

Novel cycloaddition of nitriles with monolithio- and dilithiobutadienes

J Am Chem Soc. 2002 Jun 5;124(22):6238-9. doi: 10.1021/ja0262176.

Authors

Jinglong Chen¹, Qiuling Song, Congyang Wang, Zhenfeng Xi

Affiliation

¹ Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871 China.

PMID: 12033842
DOI: 10.1021/ja0262176

Abstract

Two novel and synthetically useful reaction patterns of organolithium compounds with nitriles are reported to afford pyridine derivatives as the final products. Both 1-lithio-1,3-dienes and 1,4-dilithio-1,3-dienes, which can be easily generated in situ by lithiation of their corresponding iodo compounds, react with nitriles in the presence of HMPA to form substituted pyridines including 2,2'-bipyridines and tetrahydroisoquinolines in high yields.