Cyano Group Removal from Cyano-Promoted Aza-Diels–Alder Adducts: Synthesis and Structure–Activity Relationship of Phenanthro­indolizidines and Phenanthro­quinolizidines

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

Substituent Effects on the Iodine-Catalyzed Thermal Cyclization of 3,4-Diphenylbuta-1,3-dienyl Isocyanates: Mechanistic Studies

The thermal cyclization of 3,4-diphenylbuta-1,3-dienyl isocyanates <b>1</b>, generated <i>in situ</i> from the corresponding azides, was investigated using iodine as a catalyst. Diphenylpyridinones <b>2</b>, phenylnaphthalenes <b>3</b>, and indenes <b>4</b> 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 <b>2</b>–<b>4</b>. The mechanism of the reaction is also discussed

Substituent Effects on the Iodine-Catalyzed Thermal Cyclization of 3,4-Diphenylbuta-1,3-dienyl Isocyanates: Mechanistic Studies

The thermal cyclization of 3,4-diphenylbuta-1,3-dienyl isocyanates <b>1</b>, generated <i>in situ</i> from the corresponding azides, was investigated using iodine as a catalyst. Diphenylpyridinones <b>2</b>, phenylnaphthalenes <b>3</b>, and indenes <b>4</b> 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 <b>2</b>–<b>4</b>. The mechanism of the reaction is also discussed

Biscalix[4]arene Derivative As a Very Efficient Phase Selective Gelator for Oil Spill Recovery

A biscalixarene framework, without long alkyl chains, has been readily synthesized in three steps starting from the parent calix[4]arene. The biscalix[4]arene <b>1</b> was able to form organogels in various alcoholic solvents; furthermore, it exhibited an excellent phase selective gelation property that is potentially useful in oil spill recovery

Synthesis of 9,10-Bis-ketoenaminoanthryl and 9,10-Bis-isoxazolylanthryl Linked Biscalix[4]arenes: Atropisomers and Molecular Recognitions

An efficient synthetic pathway for the synthesis of biscalix[4]­arenes <b>5</b>–<b>10</b> using 1,3-dipolar cycloaddition reactions is reported. Biscalix[4]­arene <b>10</b> is capable of forming a complex with methyl viologen because of favorable cation−π interactions and a proper cavity size to accommodate the guest. Moreover, biscalix[4]­arenes <b>8a</b> and <b>8b</b> were found to be atropisomers at room temperature. These two conformers were unable to exchange at room temperature because of the restricted rotation of the C₉–C₁₁ or C₁₀–C₁₂ bonds of the β-amino-α,β-unsaturated ketones of anthracene

Synthesis of 9,10-Bis-ketoenaminoanthryl and 9,10-Bis-isoxazolylanthryl Linked Biscalix[4]arenes: Atropisomers and Molecular Recognitions

An efficient synthetic pathway for the synthesis of biscalix[4]­arenes <b>5</b>–<b>10</b> using 1,3-dipolar cycloaddition reactions is reported. Biscalix[4]­arene <b>10</b> is capable of forming a complex with methyl viologen because of favorable cation−π interactions and a proper cavity size to accommodate the guest. Moreover, biscalix[4]­arenes <b>8a</b> and <b>8b</b> were found to be atropisomers at room temperature. These two conformers were unable to exchange at room temperature because of the restricted rotation of the C₉–C₁₁ or C₁₀–C₁₂ bonds of the β-amino-α,β-unsaturated ketones of anthracene