- Cyano Group Removal from Cyano-Promoted Aza-Diels-Alder Adducts: Synthesis and Structure-Activity Relationship of Phenanthroindolizidines and Phenanthroquinolizidines
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Phenanthroindolizidines and phenanthroquinolizidines were concisely synthesized by the reductive decyanization of cyano-promoted intramolecular aza-Diels-Alder cycloadducts followed by aryl-aryl coupling. Cyano groups were removed from α-aminoacrylonitriles via treatment with sodium borohydride in 2-propanol in almost quantitative yields; a possible mechanism was proposed and examined using D-labeling experiments. A systematic study of the effects of the phenanthrene substitution pattern on the anticancer activity against three human cancer cell lines was discussed. (Chemical Equation Presented).
- Chang, Chi-Fen,Li, Chien-Fu,Tsai, Chia-Chen,Chuang, Ta-Hsien
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supporting information
p. 638 - 641
(2016/03/01)
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- Substituent effects on the iodine-catalyzed thermal cyclization of 3,4-diphenylbuta-1,3-dienyl isocyanates: Mechanistic studies
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The thermal cyclization of 3,4-diphenylbuta-1,3-dienyl isocyanates 1, generated in situ from the corresponding azides, was investigated using iodine as a catalyst. Diphenylpyridinones 2, phenylnaphthalenes 3, and indenes 4 were produced via intramolecular ring closure. The nature of the substituents on the phenyl rings was found to be crucial to the distribution of cyclized products 2 - 4. The mechanism of the reaction is also discussed.
- Chuang, Ta-Hsien,Chang, Wei-Yu,Li, Chien-Fu,Wen, Yu-Chia,Tsai, Chia-Chen
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supporting information; experimental part
p. 9678 - 9686
(2012/01/05)
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- Synthesis of phenanthro[9,10-b]indolizidin-9-ones, phenanthro[9,10-b] quinolizidin-9-one, and related benzolactams by Pd(OAc)2-catalyzed direct aromatic carbonylation
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Phenanthro[9,10-b]indolizidin-9-ones, phenanthro[9,10-b]-quinolizidin-9- one, and related benzolactams were synthesized by benzolactam ring formation using Pd(OAc)2-catalyzed direct aromatic carbonylation. This also constitutes a formal synthesis of the representative phenanthroindolizidine and -quinolizidine alkaloids (±)-tylophorine, (±)-antofine, and (±)-cryptopleurine. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.
- Yamashita, Satoshi,Kurono, Nobuhito,Senboku, Hisanori,Tokuda, Masao,Orito, Kazuhiko
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supporting information; experimental part
p. 1173 - 1180
(2009/07/11)
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- Synthesis, characterisation and photophysical properties of a,a-diaryl-acrylonitrile derivatives
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a,b-Diarylacrylonitrile derivatives can be prepared by two different routes: (1) the intermolecular condensation of the same arylacetonitriles (2) the condensation of arylaldehydes and arylacetonitriles with a catalytic amount of NaOCH3 at room temperature. Several a,b-diarylacrylonitrile derivatives have been synthesised in this paper and characterised. The UV-vis absorption and photoluminescent (PL) spectra of the products were investigated.
- Yue, Youfeng,Fang, Haiyan,Wang, Meijun,Wang, Zhiyuan,Yu, Mingxin
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experimental part
p. 377 - 380
(2009/12/25)
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