Reactivity and H–D Exchange Rate of the α-Methylene of Deoxyvasicinone and its Homologs

The deuterium exchange rate of the α-methylene of deoxyvasicinone (1) and mackinazolinone (2) and their seven- (3) and eight-membered (4) homologs was studied in neutral, acidic, and basic media. It was found that the exchange rate depended on the number of methylenes in the polymethylene ring and t...

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Bibliographic Details
Published in:Chemistry of natural compounds 2014-12, Vol.50 (6), p.1060-1065
Main Authors: Shakhidoyatov, Kh. M, Levkovich, M. G, Elmuradov, B. Zh, Abdullaev, N. D
Format: Article
Language:English
Subjects:
Acylation
Aldehydes
bromine
chlorides
condensation
deuterium
Medicine
Organic Chemistry
Pharmacy
Plant Sciences
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Summary:The deuterium exchange rate of the α-methylene of deoxyvasicinone (1) and mackinazolinone (2) and their seven- (3) and eight-membered (4) homologs was studied in neutral, acidic, and basic media. It was found that the exchange rate depended on the number of methylenes in the polymethylene ring and the medium. The deuterium exchange rate decreased in the order 2→1→3→4 and was slowest in media close to neutral. The results agreed with those for the reactions of 1–4 with bromine in acidic medium, condensation with substituted aromatic and heterocyclic aldehydes, and acylation by aromatic acid chlorides. Several trends in the reactivity of the tricyclic quinazolin-4-ones were discovered.
ISSN:0009-3130
1573-8388
DOI:10.1007/s10600-014-1159-6