• Reactivity of allenylphosphonates and allenylphosphine oxides toward 9-chloroacridines and acridone- A facile route to new 𝑁-substituted acridones

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    • Keywords


      Allenylphosphonate/allenylphosphine oxide; acridone; 9-chloroacridine; 9-benzyl-6-chloro-purine; Horner-Wadsworth-Emmons reaction.

    • Abstract


      Base-mediated addition of acridones to allenylphosphonates/allenylphosphine oxides (OCH2CMe2CH2O)P(O)CH=C=CR1R2 {R1 = R2 = Me (1), R1 = R2 = [−CH2−]5 (2)}, Ph2P(O)C(H)=C=CR1R2 {R1 = R2 = Me (3), R1 = R2 = [−CH2−]5 (4)} and (EtO)2P(O)C(H)=C=CMe2 (5) in DMF results in the regiospecific formation of phosphono-acridones and acridonylphosphine oxides. The acridone addition products were also obtained in the reaction of allenes 1 and 2 with 9-chloroacridine under [Pd]-catalysed conditions, along with (unexpected) 𝛼-acridinyl substituted allenes. In contrast, 9-benzyl-6-chloro-purine reacted with 1 affording a 𝛽-substituted purinone phosphonate. Allenes 1-2 did not react with acridones in the absence of base (CsF), but in the presence of Pd(OAc)2/DMF (or DMA)/pivalic acid rearranged to give 1,3-butadienes probably via [Pd]-allyl complexes. The phosphono-acridones were amenable to Horner-Wadsworth-Emmons (HWE) reaction and led to 𝑁-substituted acridones. Key products have been characterized by single-crystal X-ray crystallography.

    • Author Affiliations


      A Leela Siva Kumari1 Venu Srinivas1 K C Kumara Swamy1

      1. School of Chemistry, University of Hyderabad, Hyderabad 500 046, India
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