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Synthesis and unusual photochemistry of a highly reactive pyrimidinedione

Sergei Valer'evich Shorunov 1
Sergei Valer'evich Shorunov
, 
Matthew B Plutschack 2
Matthew B Plutschack
, 
Maksim Vladimirovich Bermeshev 1
Maksim Vladimirovich Bermeshev
, 
Ilia A Guzei 2
Ilia A Guzei
10.1016/j.mencom.2018.09.016
Published 2018-09-07
Communication , Volume 28, Issue 5, 501-502
2
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Shorunov S. V. et al. Synthesis and unusual photochemistry of a highly reactive pyrimidinedione // Mendeleev Communications. 2018. Vol. 28. No. 5. pp. 501-502.
GOST all authors (up to 50) Copy
Shorunov S. V., Plutschack M. B., Bermeshev M. V., Guzei I. A. Synthesis and unusual photochemistry of a highly reactive pyrimidinedione // Mendeleev Communications. 2018. Vol. 28. No. 5. pp. 501-502.
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TY - JOUR
DO - 10.1016/j.mencom.2018.09.016
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.09.016
TI - Synthesis and unusual photochemistry of a highly reactive pyrimidinedione
T2 - Mendeleev Communications
AU - Shorunov, Sergei Valer'evich
AU - Plutschack, Matthew B
AU - Bermeshev, Maksim Vladimirovich
AU - Guzei, Ilia A
PY - 2018
DA - 2018/09/07
PB - Mendeleev Communications
SP - 501-502
IS - 5
VL - 28
ER -
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@article{2018_Shorunov,
author = {Sergei Valer'evich Shorunov and Matthew B Plutschack and Maksim Vladimirovich Bermeshev and Ilia A Guzei},
title = {Synthesis and unusual photochemistry of a highly reactive pyrimidinedione},
journal = {Mendeleev Communications},
year = {2018},
volume = {28},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.09.016},
number = {5},
pages = {501--502},
doi = {10.1016/j.mencom.2018.09.016}
}
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MLA Copy
Shorunov, Sergei Valer'evich, et al. “Synthesis and unusual photochemistry of a highly reactive pyrimidinedione.” Mendeleev Communications, vol. 28, no. 5, Sep. 2018, pp. 501-502. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.09.016.

Abstract

The herein obtained 3-methyl-5,5-diphenylpyrimidine-2,4-(3H,5H)-dione forms upon photolysis an unusual bicyclic product, namely, 6-methyl-3,3,8,8-tetraphenyl-8,8a-dihydroimidazo[1.5-c]pyrimidine-5,7(3H,6H)-dione in 21% yield. The transformation starts with elimination of carbon monoxide and methyl isocyanate from the molecule of substrate via a ‘Type A’ photochemical process giving 3,3-diphenylazirine. Then 1,3-dipole species generated from the latter is trapped by the starting compound via a [3+2] cycloaddition.

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