Journal of Organic Chemistry p. 2246 - 2254 (1983)
Update date:2022-09-26
Topics:
Cortes, Sergio
Kohn, Harold
N3-Substituted hydantoins (1) have been shown to undergo LiAlH4 reduction (THF, room temperature, 2 days) to give 4-hydroxy-2-imidazolidinones (3) in good yields.Reduction of 3,5-disubstituted hydantoins in which an aliphatic substituent was present at nitrogen 3 led to the preferential formation of the cis adduct 3.Conversely, disubstituted hydantoins possessing an aryl moiety at nitrogen 3 gave the trans derivative 3 as the major product.Treatment of the N3-substituted hydantoins (1) under more vigorous conditions (THF, reflux, 3 days) led to selective ring opening of 1 to yield N-methylethylenediamines (7).The scope of both of these reductive processes has been explored, and explanations are offered to account for the observed results.Full spectral (infrared, 1H and 13C NMR, and mass spectra) data on all three classes of compounds (1, 3, and 7) have been collected.Together this information provides a consistent data set which is useful in structure elucidation.Moreover, various NMR aids have been discerned for the isomeric cis- and trans-4-hydroxy-2-imidazolidinones (3) which permitted stereochemical assignments for these compounds.
View MoreChangzhou Chenqiang Chemical Co., Ltd
website:http://www.cq-chem.com
Contact:+86-519-88902455
Address:Shanghuang Town, Liyang City
HANGZHOU YUNUO CHEMICAL CO.,LTD
website:http://www.yunuochem.com
Contact:0571-83715115
Address:hangzhou
suzhou BetterBioChem Co., Ltd.
website:http://www.betterbiochem.com
Contact:+86-18013506594
Address:No. 8 Building, 18 nong, Xi Yingnan Road, Pudong, Shanghai,China
Shanghai Yongyi Biotechnology Co., Ltd
Contact:+86-0512-69561955
Address:Suite 3005, City Gateway, No.398 North CaoXi Road, XuHui District, Shanghai 200030, China.
Contact:86-511-85210668 0511-85210668, 85210818, 85210898
Address:Yihai Garden E-902,NO.99 Daxi RD., Zhenjiang Jiiangsu ,China
Doi:10.1016/0040-4020(82)87014-2
(1982)Doi:10.1039/jr9350000429
(1935)Doi:10.1080/00958972.2012.719079
(2012)Doi:10.1016/S0040-4039(00)81389-1
(1983)Doi:10.1016/j.bmc.2018.11.040
(2019)Doi:10.1055/s-1983-30293
(1983)