naa a22 4500 510733786 CHVBK 20180411083002.0 cr unu---uuuuu 180411e20131101xx s 000 0 eng 10.1007/s12039-013-0498-3 doi (NATIONALLICENCE)springer-10.1007/s12039-013-0498-3 Reactivity of allenylphosphonates and allenylphosphine oxides toward 9-chloroacridines and acridone- A facile route to new N -substituted acridones [Elektronische Daten] [A KUMARI, VENU SRINIVAS, K KUMARA SWAMY] Base-mediated addition of acridones to allenylphosphonates/allenylphosphine oxides (OCH2CMe2CH2O)P(O)CH=C=CR1R2 {R1 = R2 = Me (1), R1 = R2 = [ $-{\rm CH}_{2^-}$ ]5 (2)}, Ph2P(O)C(H)= C=CR1R2 {R1 = R2 = Me (3), R1 = R2 = [ $-{\rm CH}_{2^-}$ ]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. Graphical Abstract CsF-mediated addition of acridones to allenylphosphonates and allenylphosphine oxides provides a convenient access to phosphono-acridones and acridonylphosphine oxides regiospecifically and to new N-substituted acridones by HWE reaction. Indian Academy of Sciences, 2013 Allenylphosphonate/allenylphosphine oxide nationallicence acridone nationallicence 9-chloroacridine nationallicence 9-benzyl-6-chloro-purine nationallicence Horner-Wadsworth-Emmons reaction nationallicence KUMARI A. School of Chemistry, University of Hyderabad, 500 046, Hyderabad, India aut SRINIVAS VENU School of Chemistry, University of Hyderabad, 500 046, Hyderabad, India aut KUMARA SWAMY K. School of Chemistry, University of Hyderabad, 500 046, Hyderabad, India aut Journal of Chemical Sciences Springer India 125/6(2013-11-01), 1405-1417 0974-3626 125:6<1405 2013 125 12039 https://doi.org/10.1007/s12039-013-0498-3 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s12039-013-0498-3 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- KUMARI A. School of Chemistry, University of Hyderabad, 500 046, Hyderabad, India aut NATIONALLICENCE 700 1- SRINIVAS VENU School of Chemistry, University of Hyderabad, 500 046, Hyderabad, India aut NATIONALLICENCE 700 1- KUMARA SWAMY K. School of Chemistry, University of Hyderabad, 500 046, Hyderabad, India aut NATIONALLICENCE 773 0- Journal of Chemical Sciences Springer India 125/6(2013-11-01), 1405-1417 0974-3626 125:6<1405 2013 125 12039 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer