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

Journal of Chemical Sciences

K C Kumara Swamy1¹  A Leela Siva Kumari¹  Venu Srinivas¹ 

[1] School of Chemistry, University of Hyderabad, Hyderabad 500 046, India$$

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

DOI  :  

来源: Indian Academy of Sciences

【 摘 要 】

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.

【 授权许可】

Unknown