Boranes in Synthesis. 6. A New Synthesis of .beta.-Amino Alcohols from Epoxides. Use of Lithium Amides and Aminoborane Catalysts To Synthesize .beta.-Amino Alcohols from Terminal and Internal Epoxides in High Yield

1994 ◽  
Vol 59 (25) ◽  
pp. 7746-7751 ◽  
Author(s):  
Clifford E. Harris ◽  
Gary B. Fisher ◽  
David Beardsley ◽  
Lawrence Lee ◽  
Christian T. Goralski ◽  
...  
1968 ◽  
Vol 21 (9) ◽  
pp. 2247 ◽  
Author(s):  
JW Clark-Lewis ◽  
RW Jemison

2'-Hydroxychalcones and α-alkoxy-2'-hydroxychalcones are converted by sodium borohydride in isopropanol into flav-3-enes and 3-alkoxyflav-3-enes in the convenient new synthesis which makes these flavenes readily available. Catalytic reduction of the flavenes gives the corresponding flavans or 3-alkoxyflavans in high yield, and the latter are obtained mainly in the 2,s-cis-form. The flavenes immediately give flavs lium cations in the cold when treated with acids in air, and oxidation of 5,7,3',4'-tetramethoxyflav-3-ene with benzoquinone in an acidic medium gave the flavylium salt, isolated as the ferrichloride. Reduction of 5,7,3',4'-tetramethoxy-flavylium chloride with lithium aluminium hydride gave 5,7,3',4'-tetramethoxy-flav-2-ene identical with the flavene obtained from (-)-epicatechin tetramethyl ether, and confirms an earlier investigation by Gramshaw, Johnson, and King. In its N.M.R. spectrum the heterocyclic-ring protons of this flav-2-ene give an ABX multiplet which is easily distinguished from the ABX multiplet at much lower field characteristic of flav-3-enes.


2009 ◽  
Vol 13 (08n09) ◽  
pp. 854-858 ◽  
Author(s):  
Qiang Liu ◽  
Yan-Zhi Gong ◽  
Chang-Jun Gong ◽  
Qing-Hong Li ◽  
Can-Cheng Guo

A new synthesis of μ-oxo dimeric iron(III) porphyrins from meso-tetraarylporphyrins in one-pot procedure is reported. μ-oxo dimeric iron(III) porphyrin was obtained in high yield (up to 93%) from the reaction of meso-tetraarylporphyrin with ferrous chloride in DMF at pH 8–11. Compared with other synthetic methods of μ-oxo dimeric iron(III) porphyrin from meso-tetraarylporphyrins, the one-pot procedure has higher yields of μ-oxo dimeric iron(III) porphyrins and is a simpler and more convenient procedure. In order to evaluate the range of applicability of this method, μ-oxo dimeric iron(III) porphyrins with different substituents were prepared by the reaction of the corresponding meso-tetraarylporphyrins with ferrous chloride. The results showed that it was possible to apply this one-pot procedure to the synthesis of other μ-oxo dimeric iron porphyrins in excellent yields. A mechanism for the formation of μ-oxo dimeric iron porphyrins was proposed based on the reaction intermediates characterized by HPLC and UV-vis methods.


ChemInform ◽  
2010 ◽  
Vol 25 (49) ◽  
pp. no-no
Author(s):  
G. B. FISHER ◽  
L. LEE ◽  
F. W. KLETTKE
Keyword(s):  

1970 ◽  
Vol 43 (4) ◽  
pp. 1185-1189 ◽  
Author(s):  
Itaru Okada ◽  
Kunihiro Ichimura ◽  
Rokuro Sudo
Keyword(s):  

1977 ◽  
Vol 30 (8) ◽  
pp. 1855 ◽  
Author(s):  
TG Burrowes ◽  
WR Jackson ◽  
S Faulks ◽  
I Sharp

Reaction of 5-chloromethyl-3-phenyl-4,5-dihydroisoxazole with potassium t-butoxide in dimethyl sulphoxide gives 4-phenyl-2-oxa-3- azabicyclo[3,1,0]hex-3-ene in high yield and reaction of the 5-(1?- chloroethyl) homologue gives high yields of the diastereoisomeric 6- methyl derivatives of the bicyclic system. Some unsuccessful attempts to convert these bicyclic compounds into substituted cyclo-propanols and cyclopropenes are described.


1975 ◽  
Vol 16 (24) ◽  
pp. 1969-1972 ◽  
Author(s):  
Noboru Sonoda ◽  
Goro Yamamoto ◽  
Kazuki Natsukawa ◽  
Kiyoshi Kondo ◽  
Shinji Murai

2013 ◽  
Vol 54 (47) ◽  
pp. 6307-6309 ◽  
Author(s):  
Nitin Lad ◽  
Rajiv Sharma ◽  
Victor E. Marquez ◽  
Malcolm Mascarenhas
Keyword(s):  

ChemInform ◽  
2000 ◽  
Vol 31 (47) ◽  
pp. no-no
Author(s):  
M. Antonietta Casadei ◽  
Marta Feroci ◽  
Achille Inesi ◽  
Leucio Rossi ◽  
Giovanni Sotgiu

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