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Stereoselective synthesis of 4a-fluoro-5,10-ethenobenzo[f]quinazolines via photo-Diels–Alder reaction of 5-fluoro-1,3-dimethyluracil with naphthalenes

✍ Scribed by Kazue Ohkura; Tatsuyuki Sugaoi; Ken-ichi Nishijima; Yuji Kuge; Koh-ichi Seki

Book ID: 104250913
Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 62 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)00492-6

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✦ Synopsis

UV-irradiation of a solution of 5-fluoro-1,3-dimethyluracil (5-FDMU) in aprotic media effected a stereoselective 1,4-cycloaddition reaction to give a barrelene derivative in high yield. In direct contrast, irradiation of a solution of 5-FDMU and naphthalene in a protic medium afforded 5-(1-naphthyl)uracil as the major product.

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