1989
DOI: 10.1055/s-1989-27140
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A Convenient Synthesis of 1,3-Dibenzyl-5-methylenehydantoin

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Cited by 9 publications
(6 citation statements)
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“…For 13 C NMR, chemical shifts were reported relative to CHCl 3 (77.00 ppm for 13 C NMR) as an internal reference. 2-Methylene-3,4-dihydro-2 H -naphthalen-1-one ( 1a ), 2-methylenecyclohexanone ( 1f ), 2-methylenecyclopentanone ( 1g ), 1,3-bibenzyl-5-methylenehydantoin ( 1j ), ethyl 2,3-butadienoate ( 2 ), tert -butyl 2,3-butadienoate ( 5 ), and tert -butyl 2-butynoate ( 8 ) were prepared by the reported methods.…”
Section: Methodsmentioning
confidence: 99%
“…For 13 C NMR, chemical shifts were reported relative to CHCl 3 (77.00 ppm for 13 C NMR) as an internal reference. 2-Methylene-3,4-dihydro-2 H -naphthalen-1-one ( 1a ), 2-methylenecyclohexanone ( 1f ), 2-methylenecyclopentanone ( 1g ), 1,3-bibenzyl-5-methylenehydantoin ( 1j ), ethyl 2,3-butadienoate ( 2 ), tert -butyl 2,3-butadienoate ( 5 ), and tert -butyl 2-butynoate ( 8 ) were prepared by the reported methods.…”
Section: Methodsmentioning
confidence: 99%
“…Synthesis of N,N′-Diprotected-5-methylenehydantoins. Surprisingly, with the exception of N,N′-dibenzyl-5-methylenehydantoin (9), 46,47 methods for the synthesis of usefully diprotected, N,N′diprotected-5-methylenehydantoins. Compound 9 and its previously unreported N,N′-diPMB analogue (10) were prepared from the base-catalyzed reactions of cystine hydantoin (8) 47 and the appropriate arylmethyl bromide (Scheme 2).…”
Section: Resultsmentioning
confidence: 99%
“…Surprisingly, with the exception of N,N′-dibenzyl-5-methylenehydantoin (9), 46,47 methods for the synthesis of usefully diprotected, N,N′diprotected-5-methylenehydantoins. Compound 9 and its previously unreported N,N′-diPMB analogue (10) were prepared from the base-catalyzed reactions of cystine hydantoin (8) 47 and the appropriate arylmethyl bromide (Scheme 2). The former compound was isolated pure after column chromatography in 83% yield while the latter in only 64% due to concomitant formation of the mono-N3protected-5-methylenehydantoin 11 in 15% yield.…”
Section: Resultsmentioning
confidence: 99%
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