Vinylogous Aza-Michael Addition of Urea Derivatives with p-Quinone Methides Followed by Oxidative Dearomative Cyclization: Approach to Spiroimidazolidinone Derivatives Article

Kaur, N, Singh, P, Banerjee, P. (2021). Vinylogous Aza-Michael Addition of Urea Derivatives with p-Quinone Methides Followed by Oxidative Dearomative Cyclization: Approach to Spiroimidazolidinone Derivatives . ADVANCED SYNTHESIS & CATALYSIS, 363(11), 2813-2824. 10.1002/adsc.202100077

cited authors

  • Kaur, N; Singh, P; Banerjee, P

authors

abstract

  • Herein, we report an efficient protocol for the synthesis of spiro-imidazolidinone-cyclohexadienones from p-quinone methides (p-QMs) and dialkyloxy ureas under mild conditions. The strategy follows a two-step process involving an initial vinylogous conjugate addition of urea derivatives to p-QMs, followed by oxidative dearomative cyclization of open-chain product to the projected spiro-imidazolidinones. This protocol exhibits good functional group tolerance and provides a straightforward method to access spiro-imidazolidinone-cyclohexadienones. In follow-up chemistry, we have shown the debenzylation of spiroimidazolidinones to give N-hydroxycyclic ureas. (Figure presented.).

publication date

  • June 8, 2021

published in

Digital Object Identifier (DOI)

start page

  • 2813

end page

  • 2824

volume

  • 363

issue

  • 11