Cp*RuCl-catalyzed [2 + 2 + 2] cycloadditions of alpha,omega-diynes with electron-deficient carbon-heteroatom multiple bonds leading to heterocycles

Yoshihiko Yamamoto; Keisuke Kinpara; Tomoaki Saigoku; Hideyuki Takagishi; Satoshi Okuda; Hisao Nishiyama; Kenji Itoh

doi:10.1021/ja045694g

Cp*RuCl-catalyzed [2 + 2 + 2] cycloadditions of alpha,omega-diynes with electron-deficient carbon-heteroatom multiple bonds leading to heterocycles

J Am Chem Soc. 2005 Jan 19;127(2):605-13. doi: 10.1021/ja045694g.

Authors

Yoshihiko Yamamoto¹, Keisuke Kinpara, Tomoaki Saigoku, Hideyuki Takagishi, Satoshi Okuda, Hisao Nishiyama, Kenji Itoh

Affiliation

¹ Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan. yamamoto@apchem.nagoya-u.ac.jp

PMID: 15643884
DOI: 10.1021/ja045694g

Abstract

In the presence of a catalytic amount of Cp*RuCl(cod), 1,6-diynes were allowed to react chemo- and regioselectively with electron-deficient nitriles and heterocumulenes at 60-90 degrees C to afford heterocyclic compounds. The mechanism of the ruthenium-catalyzed regioselective formations of bicyclic pyridines and pyridones were analyzed on the basis of density functional calculations. Cyclocotrimerizations of ethyl propiolate with ethyl cyanoformate or propyl isocyanate gave rise to two of the four possible pyridine or pyridone regioisomers.