A Facile, One-Pot Synthesis of Azoic Compounds and Anthraquinone Derivatives Containing Dialkyl Phosphoryl Moieties in Multicomponent Reactions

作者：Marandi Ghasem; Maghsoodlou Malek Taher^*; Heydari Reza; Habibi Khorassani Sayyed Mostafa; Kabiri Roya; Gharechahi Zahra; Ghahramaninezhad Mahbobe; Adrom Belghais

来源：Phosphorus, Sulfur, and Silicon and the Related Elements, 2010, 185(7): 1395-1403.

DOI：10.1080/10426500903061517

• 1-Amino-anthraquinone
• azoic dyes
• dialkyl acetylenedicarboxylate
• 1
• 5-diphenylcarbazone
• geometrical isomers
• stable phosphorus ylides

Protonation of the reactive 1:1 intermediates produced in the reactions between triphenylphosphine and dialkyl acetylenedicarboxylates by 1-amino-anthraquinone or 1,5-diphenylcarbazone as a core dye leads to vinyl phosphonium salts, which undergo Michael addition with conjugate base of NH compounds to produce stable phosphorus ylides as novel dyes in fairly good yields. These ylides can exist in two geometrical isomers (Z) and (E) for 3, because the negative charge of the ylide moiety of these compounds are strongly conjugated with the adjacent carbonyl group. Rotation around the carbon-carbon double bond is slow in the (Z) and (E) geometrical isomers on the NMR time scale at ambient temperature. These compounds are assigned by their IR, 1H, 13C NMR spectral data as well as their mass spectroscopic data.

• 出版日期2010