Reactions of α-phenylglycinamide with some carbonyl compounds. Formation of 5,7-diisopropyl-8,8-dimethyl-2-oxo-3-phenylimidazolidino-[1,2-c]-tetrahydro-[1,3]-oxazine, and determination of structure and stereochemistry by nuclear Overhauser effect difference measurements

α-Phenylglycinamide 5 reacts with ketones to give either the Schiff base 3 or the 4-imidazolidone 4 , but reacts with boiling isobutyraldehyde to give the bicyclic compond 6 . The structure and stereochemistry of 6 have been established by 1 H nuclear Overhauser effect difference measurements, suppo...

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Bibliographic Details
Published inCanadian journal of chemistry Vol. 67; no. 10; pp. 1560 - 1564
Main Authors Qing, Ning, Colebrook, Lawrence D, Edward, John T, Kon, Allan, Chubb, Francis L
Format Journal Article
LanguageEnglish
Published Ottawa, Canada NRC Research Press 01.10.1989
National Research Council of Canada
Subjects
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Organic chemistry
Preparations and properties
Five membered ring
Molecular structure
Aminoamide
Nitrogen heterocycle
Overhauser effect
Aldehyde
Ketone
Spiran
Bicyclic compound
Ketimine
NMR spectrum
Conformation
Oxygen nitrogen heterocycle
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Summary:α-Phenylglycinamide 5 reacts with ketones to give either the Schiff base 3 or the 4-imidazolidone 4 , but reacts with boiling isobutyraldehyde to give the bicyclic compond 6 . The structure and stereochemistry of 6 have been established by 1 H nuclear Overhauser effect difference measurements, supported by molecular mechanics calculations. Keywords: structure, stereochemistry, nuclear Overhauser effect, molecular mechanics, α-phenylglycinamide reactions.
ISSN:0008-4042
1480-3291
DOI:10.1139/v89-238