STUDY OF LITHIUM ALUMINIUM HYDRIDE REDUCTION OF 5-ACETYL-1,6-DIMETHYL-4-PHENYL-3,4-DIHYDROPYRIMIDIN-2(1H)-ONE

Dragan B. Zlatkovic, Niko S. Radulovic

DOI Number
10.2298/FUPCT1701017Z
First page
017
Last page
022

Abstract


In this paper, we investigated the LiAlH4-reduction of 5-acetyl-1,6-dimethyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one (N-methylated Biginelli compound). Following the reduction and SiO2-promoted dehydration, (Z)-5-ethylidene-1-methyl-6-methylene-4-phenyltetrahydropyrimidin-2(1H)-one was isolated as the major product (33% yield). Chromatographic separation of the reaction products also allowed us to isolate (yield in parentheses) and fully spectrally characterize: 1,6-dimethyl-4-phenyl-5-vinyl-3,4-dihydropyrimidin-2(1H)-one (20%), 5-ethyl-1,6-dimethyl-4-phenyl-3,4-dihydro-pyrimidin-2(1H)-one (9%), 5-(1-hydroxyethyl)-1,6-dimethyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one (5%). A possible mechanism explaining the formation of these products is proposed.

Keywords

Biginelli product, LiAlH4-reduction, dehydration, NMR spectroscopy, structural elucidation

Full Text:

PDF

References


Li, J.J., and Corey, E.J., 2005. Name reactions in heterocyclic chemistry, John Wiley & Sons, Hoboken, New Jersey, doi:10.1002/0471704156.

Kappe, C.O., 2000a. Eur. J. Med. Chem., 35, 1043–1052, doi:10.1016/s0223-5234(00)01189-2.

Kappe, C.O., 2000b. Acc. Chem. Res., 33, 879–888, doi:10.1021/ar000048h.

Zlatković, D.B., Radulović, N.S., 2016. RSC Adv., 6, 115058–115067, doi:10.1039/C6RA24535H.


Refbacks

  • There are currently no refbacks.


ISSN 0354-4656 (print)

ISSN 2406-0879 (online)