Electrocyclic rearrangement of pentamethylcyclooctapyrimidine-2,4-diones: reaction pathway into a 9,11-diazapentacyclo-[6.4.0.0(1,3).0(2,5).0(4,8)]dodecane system and a 9,11-diazapentacyclo [6.4.0.0(1,3).0(2,6).0(4,8)]dodecane system.

Abstract:

:Photolysis of 6-chloro-1,3-dimethyluracil and mesitylene in the presence of trifluoroacetic acid (TFA) at low temperature gave 1,3,5,7,9- and 1,3,6,8,10-pentamethylcyclooctapyrimidine-2,4-diones (1b, 1c). Sequential photoreaction of the former (1b) resulted in the formation of 9,11-diazapentacyclo[6.4.0.0(1,3).0(2,5).0(4,8)]dodecane-2,4-dione (2b) by way of 9-exo-methylene derivative (7b) and cyclobutaquinazoline (8b). On the other hand, UV-irradiation of 1c led to the bond shift isomer (5c) whose photolysis in the presence of TFA gave rise to the formation of the [6.4.0.0(1,3).0(2,6).0(4,8)]dodecane isomer (3c).

journal_name

Photochem Photobiol

authors

Ohkura K,Nishijima K,Seki K

doi

10.1562/0031-8655(2001)074<0385:eropdr>2.0.co;2

subject

Has Abstract

pub_date

2001-09-01 00:00:00

pages

385-90

issue

3

eissn

0031-8655

issn

1751-1097

journal_volume

74

pub_type

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