An Unusual Synthesis of Arylazo Substituted Azaphospha [5, 1-A] Quinolines by Reaction of N-Alkylarylazo Quinolinium Salts with Phosphorus Trichloride

Abstract

1,2-Dialkyl-3-arylazo quinolinium chloride 1 having N-methylene group activated by the insertion of arylazo site react with phosphorus trichloride to give N-(dichloro phosphinomethylene) quinolinium ylide 2 . The site of the reaction is determined by the relative activation of 1- and 2-methylene groups, in the absence of sufficient activation of N-methylene group, reactions occur at the 2-methylene group to give dichloro phosphinylated anhydrobases 5 and 11.

Keywords:

• 1-Alkyl-2-(dichlorophosphinomethylene) Quinolinium Anhydrobases
• 2,4,6-trialkyl-3-arylazo Quinolines
• N-alkyl Quinolinium Halides
• N-(dichloro Phosphino Methylene) Quinolinium Ylides