VERSATILE PHOTOREARRANGEMENT OF PHOTOCYCLOADDUCTS FROM 5-FLUORO-1,3-DIMETHYLURACIL AND NAPHTHALENE

被引：1

作者：

Ohkura, Kazue ^{[1
]}

Akizawa, Hiromichi ^{[1
]}

Kudo, Mikiko ^{[1
]}

Ishihara, Tetsuya ^{[1
]}

Oshima, Nobuhiro ^{[1
]}

Seki, Koh-ichi ^{[2
]}

机构：

[1] Hlth Sci Univ Hokkaido, Fac Pharmaceut Sci, Ishikari, Hokkaido 0610293, Japan

[2] Hokkaido Univ, Cent Inst Radio Isotope Sci, Kita Ku, Sapporo, Hokkaido 0600815, Japan

来源：

HETEROCYCLES | 2012年 / 84卷 / 02期

关键词：

Valence Isomerization; Di-pi-methane Rearrangement; Benzopyrimidobarrelene; Benzopyrimidosemibullvalene; Naphthocyclobutapyrimidine; DI-PI-METHANE; STEREOSELECTIVE-SYNTHESIS; PHOTOCHEMISTRY; REARRANGEMENTS; BENZENE; FURAN;

D O I：

10.3987/COM-11-S(P)83

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Direct UV-irradiation of 5-fluoro-1,3-dimethyluracil (5-FDMU) and naphthalene (1) with a 500 W high-pressure mercury lamp in a degassed Pyrex tube (lambda, > 300 nm) predominantly afforded benzopyrimidobarrelene derivative (2) through 1,4-addition, while irradiation in the presence of piperylene in singlet excited states preferentially afforded naphthocyclobuta- pyrimidine derivative (3) via 1,2-addition. Upon 254 nm light-irradiation of 2 gave rise to the formation of benzopyrimidosemibullvalene (4) in fair yields. The reaction pathway for the formation of 4 is reasonably explained in the terms of di-pi-methane rearrangement. Adduct 3 was newly converted to the corresponding barrelene derivative (2) by long-wave-length irradiation in the presence of a triplet sensitizer.

引用

页码：1057 / 1065

页数：9

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