Gold-catalyzed formation of pyrrolo- and indolo-oxazin-1-one derivatives: The key structure of some marine natural products
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, cilt.11, ss.897-905, 2015 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 11
- Basım Tarihi: 2015
- Doi Numarası: 10.3762/bjoc.11.101
- Dergi Adı: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.897-905
- Anahtar Kelimeler: alkyne cyclization, gold-catalyzed reaction, indolo-oxazin-1-one, marine natural products, pyrrolo-oxazin-1-one, LAMELLARIN-O, LUKIANOL-A, SELECTIVE SYNTHESIS, ACETYLENIC ACIDS, ALKALOIDS, CYCLIZATION, CYCLOISOMERIZATION, 1,3-DIENES, REACTIVITY, HYDRATION
- Orta Doğu Teknik Üniversitesi Adresli: Evet
Özet
Various N-propargylpyrrole and indolecarboxylic acids were efficiently converted into 3,4-dihydropyrrolo- and indolo-oxazin-1-one derivatives by a gold(III)-catalyzed cyclization reaction. Some of the products underwent TFA-catalyzed double bond isomerization and some did not. Cyclization reactions in the presence of alcohol catalyzed by Au(I) resulted in the formation of hemiacetals after cascade reactions.