Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
Acid-Catalyzed Photoreaction of 6-Chloro-1,3-dimethyluracil in Frozen Benzene: Formation of Novel Cycloadducts, Tetrahydropentaleno[1,2-e]pyrimidine-2,4-dione Derivatives
Kazue OhkuraYukari NoguchiKoh-ichi Seki
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1997 Volume 26 Issue 1 Pages 99-100

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Abstract

Contrasting to the photoreaction of 6-chloro-1,3-dimethyluracil in benzene at ambient temperature in the presence of trifluoroacetic acid, whereby 1,3-dimethylcyclooctapyrimidine was produced as a sole cycloadduct, the similar photoreaction in frozen benzene at −15 ∼ −20 °C proceeded quite differently to give three novel photocycloadducts, 7-chloro-1,3-dimethyl-4b,5,7a,8-tetrahydropentaleno[1,2-e]pyrimidine-2,4-dione, 5-chloro-1,3-dimethyl-4b,7,7a,8-tetrahydropentaleno[1,2-e]pyrimidine-2,4-dione, and 6-chloro-10,12-diazapentacyclo[6.4.0.01,3.02,5.04,8]dodecane-9,11-dione.

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© 1997 The Chemical Society of Japan
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