A comparative study of the interaction of salicylaldehydes with phosphonoacetates under Knoevenagel reaction conditions. Synthesis of 1,2-benzoxaphosphorines and their dimers
Тип публикации: Journal Article
Дата публикации: 1996-09-01
SCImago Q3
WOS Q3
БС2
SJR: 0.36
CiteScore: 3.7
Impact factor: 2.1
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Краткое описание
The reaction of salicylaldehydes 5 with phosphonoacetates 6 gives the coumarin-3-phosphonates 7 and the 1,2-benzoxaphosphorine-3-carboxylates 8 in yields and 7:8 ratios depending on the reaction conditions. A mechanistic explanation is given for the stereoselectivity of these reactions. Irradiation of compounds 8 or direct exposure to sunlight causes their head-to-tail dimerization, giving the dimers 11 and in one case its phosphorous epimer 12 . Their structure was confirmed by x-ray crystallographic analyses. Some spectroscopic characteristics of diagnostic importance for compounds 7, 8, 11 and 12 are also discussed.
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Bojilova A. et al. A comparative study of the interaction of salicylaldehydes with phosphonoacetates under Knoevenagel reaction conditions. Synthesis of 1,2-benzoxaphosphorines and their dimers // Tetrahedron. 1996. Vol. 52. No. 38. pp. 12597-12612.
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Bojilova A., Nikolova R., Ivanov C., Rodios N. A., Terzis A., Raptopoulou C. P. A comparative study of the interaction of salicylaldehydes with phosphonoacetates under Knoevenagel reaction conditions. Synthesis of 1,2-benzoxaphosphorines and their dimers // Tetrahedron. 1996. Vol. 52. No. 38. pp. 12597-12612.
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TY - JOUR
DO - 10.1016/0040-4020(96)00748-X
UR - https://doi.org/10.1016/0040-4020(96)00748-X
TI - A comparative study of the interaction of salicylaldehydes with phosphonoacetates under Knoevenagel reaction conditions. Synthesis of 1,2-benzoxaphosphorines and their dimers
T2 - Tetrahedron
AU - Bojilova, Anka
AU - Nikolova, R.
AU - Ivanov, Christo
AU - Rodios, Nestor A.
AU - Terzis, A.
AU - Raptopoulou, C. P.
PY - 1996
DA - 1996/09/01
PB - Elsevier
SP - 12597-12612
IS - 38
VL - 52
SN - 0040-4020
SN - 1464-5416
ER -
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@article{1996_Bojilova,
author = {Anka Bojilova and R. Nikolova and Christo Ivanov and Nestor A. Rodios and A. Terzis and C. P. Raptopoulou},
title = {A comparative study of the interaction of salicylaldehydes with phosphonoacetates under Knoevenagel reaction conditions. Synthesis of 1,2-benzoxaphosphorines and their dimers},
journal = {Tetrahedron},
year = {1996},
volume = {52},
publisher = {Elsevier},
month = {sep},
url = {https://doi.org/10.1016/0040-4020(96)00748-X},
number = {38},
pages = {12597--12612},
doi = {10.1016/0040-4020(96)00748-X}
}
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MLA
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Bojilova, Anka, et al. “A comparative study of the interaction of salicylaldehydes with phosphonoacetates under Knoevenagel reaction conditions. Synthesis of 1,2-benzoxaphosphorines and their dimers.” Tetrahedron, vol. 52, no. 38, Sep. 1996, pp. 12597-12612. https://doi.org/10.1016/0040-4020(96)00748-X.
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