Model reactions for a synthesis of streptamine based on the diamination of nitrocyclitol acetates

1968 ◽  
Vol 46 (17) ◽  
pp. 2793-2797 ◽  
Author(s):  
Hans H. Baer ◽  
Margaret C. T. Wang
Keyword(s):  
Sodium Borohydride ◽  
Catalytic Hydrogenation ◽  
Borohydride Reduction ◽  
Permanganate Oxidation ◽  
Sodium Borohydride Reduction ◽  
Model Reactions

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).

Quaternization and sodium borohydride reduction of N-(4-pyridylcarbonylamino)-1,2,3,6-tetrahydropyridine. Synthesis of N-amino-1,2,3,6-tetrahydropyridines

1979 ◽  
Vol 57 (22) ◽  
pp. 2981-2985 ◽  
Author(s):  
K. Redda ◽  
L. A. Corleto ◽  
E. E. Knaus
Keyword(s):  
Methyl Iodide ◽  
Sodium Borohydride ◽  
Catalytic Hydrogenation ◽  
Quaternary Salt ◽  
Borohydride Reduction ◽  
Pharmacological Activities ◽  
Sodium Borohydride Reduction

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.

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
Keyword(s):  
Sodium Borohydride ◽  
Catalytic Hydrogenation ◽  
Room Temperature ◽  
Periodic Acid ◽  
Metal Hydrides ◽  
Borohydride Reduction ◽  
Complex Metal ◽  
Sodium Borohydride Reduction ◽  
A Minor ◽  
Minor Quantity

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.

1,2-Benzothiazines. II. The Preparation and Sodium Borohydride Reduction of 3-Acyl-2H-1,2-benzothiazin-4(3H)-one 1,1-Dioxides1

1965 ◽  
Vol 30 (7) ◽  
pp. 2241-2246 ◽  
Author(s):  
Harold Zinnes ◽  
Roger A. Comes ◽  
Francis R. Zuleski ◽  
Albert N. Caro ◽  
John Shavel
Keyword(s):  
Sodium Borohydride ◽  
Borohydride Reduction ◽  
Sodium Borohydride Reduction
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