Reaction of cis- and trans-4-alkoxycarbonylamino-3-hydroxythiophans with thionyl chloride

1975 ◽  
Vol 11 (3) ◽  
pp. 290-293
Author(s):  
S. D. Mikhno ◽  
T. M. Filippova ◽  
N. S. Kulachkina ◽  
I. G. Razumova ◽  
V. M. Berezovskii
Keyword(s):  
Thionyl Chloride ◽  
Cis And Trans

Study of the reaction of cis- and trans-4-acylamino-3-hydroxythiophans with thionyl chloride

1975 ◽  
Vol 11 (2) ◽  
pp. 155-158
Author(s):  
S. D. Mikhno ◽  
T. M. Filippova ◽  
N. S. Kulachkina ◽  
I. G. Razumova ◽  
V. A. Zamureenko ◽  
...  
Keyword(s):  
Thionyl Chloride ◽  
Cis And Trans

Preparation of antidotes for anticholinesterase poisoning. IV. Synthesis and protective effectiveness of 2′-(cis- and trans-2″-hydroxycyclohexyl)aminoethyl 1-phenylcyclopentanecarboxylate hydrochlorides

1970 ◽  
Vol 48 (9) ◽  
pp. 1377-1382 ◽  
Author(s):  
R. A. B. Bannard ◽  
J. H. Parkkari
Keyword(s):  
Thionyl Chloride ◽  
Similar Reaction ◽  
Cis And Trans ◽  
Hydrolysis Of ◽  
Protective Effectiveness

The syntheses of cis- and trans-2-aminocyclohexanols and of cis- and trans-2-ethylaminocyclohexanols are described. The cis isomers were prepared by treatment of the corresponding trans-2-acetamidocyclohexanols with thionyl chloride followed by hydrolysis of the resulting intermediate oxazolines. The 2-aminocyclohexanols were converted to 2′-(cis- and trans-2″-hydroxycyclohexyl)aminoethyl 1-phenyl-cyclopentanecarboxylate hydrochlorides (1 and 2, R = H) by treatment with 2′-bromoethyl 1-phenyl-cyclopentanecarboxylate, but attempts to convert the 2-ethylaminocyclohexanols to 1 and 2 (R = C2H5) by a similar reaction were unsuccessful. The anticholinesterase activities of several of the compounds are discussed, as are the potencies of 1 and 2 (R = H) in protecting mice and rats from sarin poisoning.

Aminocyclitols. III. Synthesis of diaminocyclohexanediols

1979 ◽  
Vol 57 (14) ◽  
pp. 1870-1876 ◽  
Author(s):  
Gerry Kavadias ◽  
Robert Droghini
Keyword(s):  
Thionyl Chloride ◽  
Sodium Azide ◽  
Ring Opening ◽  
Boron Trifluoride ◽  
Boron Trifluoride Etherate ◽  
Reaction Sequence ◽  
Acidic Hydrolysis ◽  
Ring Opening Reactions ◽  
Cis And Trans ◽  
Hydrolysis Of

Reaction of N,N′-diethoxycarbonyl-2,5-dideoxystreptamine (1b) with thionyl chloride produced the iminoether dihydrochloride 8 which, upon simple treatment with water gave the di-N,O-carbonyl compound 9. Acidic hydrolysis of 9 yielded the aminocyclitol 2a. Alternatively, 2a was prepared from N,N′-dibenzoyl-2,5-dideoxystreptamine (1c) via the oxazoline 10 followed by acidic hydrolysis. Treatment of 1c with triethyl orthoacetate in the presence of boron trifluoride etherate produced the oxazoline 11 and the latter product was hydrolyzed to give 3a. By the same reaction sequence, 1e and 1h were converted to the oxazolines 12 and 13 which upon acidic hydrolysis provided the enantiomeric aminocyclitols 4 and 5. Ring-opening reactions of cis- and trans-1,4-diepoxycyclohexanes (14 and 16) with sodium azide to the diazido compounds 15 and 17, followed by reduction, afforded the aminocyclitols 6 and 7.

Trypanocidal Structure-Activity Relationshipfor Cis- and Trans-methylpluviatolide

Planta Medica ◽  
2008 ◽  
Vol 74 (03) ◽  
Author(s):  
R Silva ◽  
J Saraiva ◽  
S Albuquerque ◽  
C Curti ◽  
PM Donate ◽  
...  
Keyword(s):  
Structure Activity ◽  
Cis And Trans
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