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Volumn 62, Issue 43, 2006, Pages 10152-10161

Synthesis and utility of new amine/nucleobase addition products of allenylphosphonates

Author keywords

Allenylphosphonates; Enaminophosphonates; HWE reaction; Mitsunobu reaction; Nucleobase; X ray structure

Indexed keywords

(ENAMINO) 1,3 BUTADIENE DERIVATIVE; (ENAMINO)ALLYL PHOSPHONATE; ADENINE; ALLENE DERIVATIVE; ALLENYL PHOSPHONATE DERIVATIVE; ALLYL PHOSPHONATE; AMINE; AMMONIA; FUNCTIONAL GROUP; NUCLEIC ACID BASE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG; VINYL PHOSPHONATE;

EID: 33748429549     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.08.034     Document Type: Article
Times cited : (44)

References (77)
  • 1
    • 33748434154 scopus 로고    scopus 로고
    • Selected recent reviews:
  • 9
    • 22944485617 scopus 로고    scopus 로고
    • Ma S. Chem. Rev. 105 (2005) 2829
    • (2005) Chem. Rev. , vol.105 , pp. 2829
    • Ma, S.1
  • 10
    • 34250656871 scopus 로고    scopus 로고
    • Functionalized Fluorinated Allenes
    • Soloshonok V. (Ed), ACS Publications Division and Oxford University Press, Washington, DC
    • Hammond G.B. Functionalized Fluorinated Allenes. In: Soloshonok V. (Ed). Fluorine-Containing Synthons (2005), ACS Publications Division and Oxford University Press, Washington, DC
    • (2005) Fluorine-Containing Synthons
    • Hammond, G.B.1
  • 11
    • 33748430727 scopus 로고    scopus 로고
    • Some recent references:
  • 31
    • 33748420718 scopus 로고    scopus 로고
    • Selected recent references:
  • 39
    • 33748422872 scopus 로고    scopus 로고
    • For examples of nucleobase appended phosphonates and their biological activity see:
  • 40
    • 0142171945 scopus 로고    scopus 로고
    • Synthesis and Biological Activity of Isopolar Acyclic Nucleotide Analogs
    • Chu C.K. (Ed), Elsevier, Amsterdam
    • Holy A. Synthesis and Biological Activity of Isopolar Acyclic Nucleotide Analogs. In: Chu C.K. (Ed). Recent Advances in Nucleosides: Chemistry and Chemotherapy (2002), Elsevier, Amsterdam
    • (2002) Recent Advances in Nucleosides: Chemistry and Chemotherapy
    • Holy, A.1
  • 48
    • 0004087670 scopus 로고
    • Rappaport Z. (Ed), Wiley, Chichester, UK
    • In: Rappaport Z. (Ed). The Chemistry of Enamines (1994), Wiley, Chichester, UK
    • (1994) The Chemistry of Enamines
  • 50
    • 33748424453 scopus 로고    scopus 로고
    • Amination of nonphosphorylated allenes:
  • 64
    • 33748421583 scopus 로고    scopus 로고
    • Compounds 3a-b are known; compounds 3c-d were prepared similarly. See:
  • 66
    • 33748416390 scopus 로고    scopus 로고
    • Satish Kumar, N. Ph.D. Thesis, University of Hyderabad, India, 2004.
  • 67
    • 33748422572 scopus 로고    scopus 로고
    • Single crystal X-ray data were collected on a Bruker AXS SMART diffractometer using Mo Kα (λ=0.71073 Å) radiation. The structures were solved and refined by standard methods:
  • 70
    • 33748425340 scopus 로고    scopus 로고
    • note
    • (Z)- and (E)-α-Alkenyl phosphonates with nucleobases like adenine, guanine, thymine, etc., are prepared by reacting alkynyl phosphonates with nucleobase+KO-t-Bu+18-C-6 (Ref. 7h).
  • 71
    • 33748437296 scopus 로고    scopus 로고
    • note
    • The allene 3a also reacts, but 3c yields more stable products.
  • 72
    • 84943429076 scopus 로고    scopus 로고
    • For possible adenine-N(7)H tautomer depicted in Scheme 3, see: Shaw, G. Purines. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Potts, K. T. (Volume Editor); Pergamon: Oxford, UK, 1984; Vol. 5, Section 4.09, p 520.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.