Keywords
1
3
4-trimethylglycolurils
Birum-Oleksyszyn reaction
diastereomers
one-pot synthesis.
phosphonates
triphenyl phosphite
Abstract
The reaction of 1,3,4-trimethylglycoluril, aliphatic aldehydes and triphenyl phosphite in the presence of methanesulfonic acid affords new phosphorus-containing derivatives of glycoluril. The thus formed diastereomers of 1-[1-(diphenoxy-phosphoryl)alkyl]-3,4,6-trimethylglycolurils were separated by reverse-phase HPLC
References
.
Kravchenko A.N., Sigachev A.S., Maksareva E.Y., Gazieva G.A., Trunova N.S., Lozhkin B.V., Pivina T.S., Il’in M.M., Lyssenko K.A., Nelyubina Y.V., Davankov V.A., Lebedev O.V., Makhova N.N., Tartakovsky V.A.
Russian Chemical Bulletin,
2005
.
Kuptsova A.O., Vinogradova E.E., Kravchenko A.N., Gazieva G.A.
Russian Chemical Bulletin,
2022
.
Baranov V.V., Vol'khina T.N., Kolotyrkina N.G., Kravchenko A.N.
Mendeleev Communications,
2022
.
Moreno-Cinos C., Sassetti E., Salado I.G., Witt G., Benramdane S., Reinhardt L., Cruz C.D., Joossens J., Van der Veken P., Brötz-Oesterhelt H., Tammela P., Winterhalter M., Gribbon P., Windshügel B., Augustyns K., et. al.
Journal of Medicinal Chemistry,
2018
.
Moradi S., Zolfigol M.A., Zarei M., Alonso D.A., Khoshnood A.
ChemistrySelect,
2018
.
Skoreński M., Milewska A., Pyrć K., Sieńczyk M., Oleksyszyn J.
Journal of Enzyme Inhibition and Medicinal Chemistry,
2018
.
Sal’keeva L.K., Taishibekova E.K., Bakibaev A.A., Minaeva E.V., Makin B.K., Sugralina L.M., Sal’keeva A.K.
Russian Journal of General Chemistry,
2017
.
Ceradini D., Shubin K.
RSC Advances,
2021
.
Birum G.H.
Journal of Organic Chemistry,
1974
.
Sinitsyna A.A., Il’yasov S.G., Chikina M.V., Eltsov I.V., Nefedov A.A.
Chemical Papers,
2019
.
Mikroyannidis J.A.
Phosphorous and Sulfur and the Related Elements,
1982
.
Synthesis of trialkyl semithioglycolurils from alkylthiourea-glyoxal cyclic adducts and dialkylureas
Galochkin A.A., Baranov V.V., Kolotyrkina N.G., Kravchenko A.N.
Mendeleev Communications,
2022
.
Ramos-Llorca A., Decraecker L., Cacheux V.M., Zeiburlina I., De bruyn M., Battut L., Moreno-Cinos C., Ceradini D., Espinosa E., Dietrich G., Berg M., De Meester I., Van Der Veken P., Boeckxstaens G., Lambeir A., et. al.
Frontiers in Chemistry,
2023
.
Kalichkina L.E., Fateev A.V., Krivolapenko P.K., Isakova K.A., Knyazev A.S., Malkov V.S., Bakibaev A.A., Tuguldurova V.P.
Magnetochemistry,
2022