ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

A search for synthetic routes to tetrabenzylglycoluril

Anastasia A. Sinitsyna, Sergey G. Il’yasov, Maya V. Chikina, Ilia V. Eltsov, and Andrey A. Nefedov

Laboratory of High-Energy Compounds Synthesis, Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences (IPCET SB RAS), Biysk, Russia

E-mail: ilysow@ipcet.ru

Received: 5 May 2019  Accepted: 17 September 2019

Abstract:

In this study, a search for synthetic routes to never-before-seen tetrabenzylglycoluril was made and two synthetic strategies were examined: condensation of 1,3-dibenzylurea with glyoxal, and N-alkylation of glycoluril and its disubstituted derivative. The first synthetic approach furnished only a condensation product, 3,3′-bi(6,8-dibenzyl-2,4-dioxa-9,8-diazabicyclo[3.3.0]octan-7-one, bearing the dioxolane moiety, in 24% yield. The second method in which 2,6-dibenzylglycoluril was reacted with BnCl in acetonitrile in the presence of KOH for 3 h afforded the target product tetrabenzylglycoluril in over 60% yield.

Keywords: Glycoluril; Glyoxal; Condensation; Benzylation; Tetrabenzylglycoluril

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-019-00941-4

Chemical Papers 74 (3) 1019–1025 (2020)