Flavan derivatives. XXXIII. 2-Methoxyflavan-3,4-dione and 2-Methoxyflavan-3,4-diol derivatives

1972 ◽  
Vol 25 (4) ◽  
pp. 857 ◽  
Author(s):  
JW Clark-Lewis ◽  
I Dainis ◽  
EJ McGarry ◽  
MI Baig

Sodium borohydride reduction of 3-hydroxy-7-benzyloxy-2,3,4'-trimethoxy-flavanone and of 3-hydroxy-2,3,7,4'-tetramethoxyflavanone is shown to yield mainly trans-trans-2-methoxyflavan-3,4-dials, a novel class of flavan derivatives. The 7-benzyloxy hemiacetal also gave a minor quantity of the cis-cis-2-methoxyflavan-3,4-dial and less of the corresponding 2,3-cis-flavan-3,4-trans-dial. Catalytic hydrogenation over palladium, or reduction with complex metal hydrides at room temperature or above, converted the hemiacetals into the flavonols from which they were originally prepared by oxidation with periodic acid in methanol.

1968 ◽  
Vol 46 (17) ◽  
pp. 2793-2797 ◽  
Author(s):  
Hans H. Baer ◽  
Margaret C. T. Wang

Treatment of trans,trans-2-nitro-1,3-cyclohexanediol diacetate with ammonia followed by acetylation gives trans,trans 1,3-diacetamido-2-nitrocyclohexane (4). Catalytic hydrogenation of 4 and subsequent acetylation lead to trans,trans-2,6-diacetamidocyclohexylamine (5) and trans,trans-1,2,3-triacetamidocyclohexane (6), respectively. Permanganate oxidation of 4 affords cis-2,6-diacetamidocyclohexanone (7; 2,4-dinitrophenylhydrazone, 8). Sodium borohydride reduction of 7 produces trans,trans-2,6-diacetamidocyclohexanol (9; O-acetate, 10).


1979 ◽  
Vol 57 (22) ◽  
pp. 2981-2985 ◽  
Author(s):  
K. Redda ◽  
L. A. Corleto ◽  
E. E. Knaus

Reaction of N-(4-pyridylcarbonylamino)-1,2,3,6-tetrahydropyridine (2a) with methyl chloroformate afforded the quaternary salt 3a whereas reaction with methyl iodide gave a mixture of 3b and 6. Sodium borohydride reduction of 3a using methanol at −65 °C gave the N-methoxycarbonyl-1,2-dihydropyridine 4a whereas reduction using ethanol at 0 °C gave the 1,2,3,6-tetrahydropyridine 4b. Reduction of 3b and 6 gave rise to a mixture of 4c and 7. Catalytic hydrogenation of 4b and 4c afforded the respective piperidyl derivatives 10 and 11. The pharmacological activities of the products are presented.


Author(s):  
Zuochao Wang ◽  
Xueke Wu ◽  
Yingnan Qin ◽  
Yi Han ◽  
Dan Zhang ◽  
...  

A new fluoride vacancy of tradition metal material (FV-LaF3-x nanosheets) is rationally designed and synthesized by sodium borohydride reduction at room temperature, which improves the nitrogen reduction performance due to multi-step promotion.


2015 ◽  
Vol 39 (2) ◽  
pp. 1430-1437 ◽  
Author(s):  
Rajarshi Kashyap ◽  
Dhruba Joyti Talukdar ◽  
Sanjay Pratihar

An efficient, sustainable and green procedure for the synthesis of selective orthorhombic iron(oxalate) capped Fe–Cu bimetallic oxide nanomaterial [Fe(ox)Fe–CuOx] was developed using a sodium borohydride reduction of iron(ii) salt in the presence of oxalic acid at room temperature followed by addition of copper sulfate in water.


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