Electrocyclic Rearrangement of Pentamethylcyclooctapyrimidine-2,4-diones: Reaction Pathway into a 9,11-Diazapentacyclo-[6.4.0.01,3.02,5.04,8]dodecane System and a 9,11-Diazapentacyclo [6.4.0.01,3.02,6.04,8]dodecane System†,¶

Kazue Ohkura; Ken-ichi Nishijima; Koh-ichi Seki

doi:10.1562/0031-8655(2001)074<0385:EROPDR>2.0.CO;2

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1 September 2001 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

Kazue Ohkura, Ken-ichi Nishijima, Koh-ichi Seki

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Photochemistry and Photobiology, 74(3):385-390 (2001). https://doi.org/10.1562/0031-8655(2001)074<0385:EROPDR>2.0.CO;2

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).

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Kazue Ohkura, Ken-ichi Nishijima, and Koh-ichi Seki "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," Photochemistry and Photobiology 74(3), 385-390, (1 September 2001). https://doi.org/10.1562/0031-8655(2001)074<0385:EROPDR>2.0.CO;2

Received: 2 February 2001; Accepted: 1 May 2001; Published: 1 September 2001

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