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Synthesis of glycolurils and hydantoins by reaction of urea and 1, 2‐dicarbonyl compounds using etidronic acid as a “green catalyst”
Author(s) -
Bakibaev Abdigali A.,
Uhov Artur,
Malkov Victor,
Panshina Svetlana
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.4132
Subject(s) - chemistry , catalysis , urea , reaction conditions , condensation reaction , etidronic acid , condensation , aqueous solution , organic chemistry , medicine , physics , osteoporosis , thermodynamics , endocrinology
Most of the known methods for the synthesis of heterocyclic compounds have disadvantages, such as a long reaction time and aggressive conditions. We have developed a new, rather simple and efficient method for the synthesis of a number of glycoluryls and hydantoins in water using a etidronic acid (HEDP) as “Green catalyst.” So, for the first time, the condensation reaction of ureas with 1, 2‐dicarbonyl compounds was carried out in the presence of HEDP. Also based on NMR studies, a chemism of these reactions, which is stepwise, is proposed. It has been established that the optimal conditions for the synthesis of glycoluryls and hydantoins using HEDP are: temperature 80°C‐90°C, 40‐20 minutes, and the ratio of urea and HEDP is 1:1. In all cases, the remaining aqueous filtrate containing HEDP after the reaction can be reused for other cycles synthesis of glycoluril and other compounds, because HEDP is not converted during the reaction.