Synthesis of 6-substituted pyrimidines by the wittig reaction. III . Via 2-amino-4-hydroxy-5-phenylbutyl-6-pyrimidylmethyl triphenyl phosphonium bromide

1966 ◽  
Vol 3 (3) ◽  
pp. 324-327 ◽  
Author(s):  
B. R. Baker ◽  
Johannes H. Jordaan
Author(s):  
Md. Saiful Islam ◽  
Ikuo Ueda

5-ethoxycarbonyl-2-(alkyloraryl)-4-(alkyloraryl)-2-cylopenten-1-one and 2-ethoxycar-bonyl-5-(alkyl or aryl)-3-(alkyl or aryl)-2- cyclopenten-1-one derivatives and ethyl-6-(alkyl or aryl)-3-(alkyl or aryl)-6-oxo-2,4-hexadienoate derivatives have been prepared by a single step reaction between [2-ethoxy-3-(4-subsituted phenyl)-2-propenylidene triphenyl phosphonium bromides and bifunctional carbonyl compounds e.g glyoxal in presence of a base. The mechanism of the formation of the products is also proposed. Key words: Wittig Reaction, Triphenyl phosphonium bromide, Hexadienoate, Cyclopentanoate Dhaka Univ. J. Pharm. Sci. Vol.3(1-2) 2004 The full text is of this article is available at the Dhaka Univ. J. Pharm. Sci. website


Chemosphere ◽  
2017 ◽  
Vol 167 ◽  
pp. 44-52 ◽  
Author(s):  
Mohamed Khalid AlOmar ◽  
Mohammed Abdulhakim Alsaadi ◽  
Maan Hayyan ◽  
Shatirah Akib ◽  
Muhammad Ibrahim ◽  
...  

1983 ◽  
Vol 61 (6) ◽  
pp. 1053-1059 ◽  
Author(s):  
J. Balsevich

The preparation of various deuterium labelled 9- and/or 10-oxygenated derivatives of geraniol, geranial, nerol, and neral is described. Wittig reaction of the tetrahydropyranyl ethers of (E)- and (Z)-1,1-dideutero-6-(triphenylphosphonium)-3-methyl-2-hexen-1-ol iodides (23 and 24) with the tetrahydropyranyl ethers of hydroxyacetone and 1,3-dihydroxyacetone afforded, after deprotection, C-1 dideuterated 9-hydroxygeraniol, 9-hydroxynerol, 9,10-dihydroxygeraniol, and 9,10-dihydroxynerol of high isomeric purity. Selective oxidation of these products allowed for the preparation of the corresponding derivatives possessing an aldehyde functionality at C-9 or C-1 and C-9. Wittig reaction of 23 and 24 with pyruvaldèhyde dimethyl acetal followed by acidic hydrolysis afforded C-1 dideuterated 10-oxogeraniol and 10-oxonerol, oxidation of which yielded C-1 deuterated 10-oxogeranial and 10-oxoneral. Wittig reaction of (E)- and (Z)-1,1-dideutero-6-(triphenyl-phosphonium)-3-methyl-2-hexen-1-ol iodides (49 and 50) with 1,1,3,3-tetraethoxyacetone afforded C-1 dideuterated 9,9,10,10-tetraethoxygeraniol and 9,9.10,10-tetraethoxynerol, oxidation of which provided C-1 deuterated 9,9,10,10-tctraethoxygeranial and 9,9,10,10-tetraethoxyneral.


1988 ◽  
Vol 41 (1) ◽  
pp. 19 ◽  
Author(s):  
A Jefferson ◽  
MV Sargent ◽  
S Wangchareontrakul

The presence of 3-(10′-phenyldecyl)-(2) (2%), 3-(12′-phenyldodecyl)- (3) (6%), 4-(10′-phenyldecyl)-(4) (0.3%) and 4-(12′-phenyldodecyl)- benzene-1,2-diol (5) (0.3%) in Burmese lac , the sap of Melanorrhoea usitata Wall has been confirmed by the synthesis of these compounds and a comparison of the gas chromatographic retention times and the mass spectral characteristics of their bis-O-( trimethylsilyl ) derivatives with the derivatives of the natural products. Typically, 3,4- bis ( benzyloxy ) benzaldehyde (7) on Wittig reaction with triphenyl (11- phenylundecyl ) phosphonium bromide (20) and subsequent catalytic hydrogenation of the resultant olefin gave compound (5) in 59% overall yield.


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