К 70-летию академика юнусова марата сабировича

 

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89
KINETIC RESOLUTION 
OF SPIROCYCLOPROPANE-1,3’-OXINDOLES 
 
N. Sucman
 
Institute of Chemistry, Academy of Sciences of Moldova, Academiei 3,
MD-2028, Chisinau, Moldova 
[e-mail] and [e-mail]
 
The issue of chirality has become increasingly important to the pharmaceutical, chemical, and 
agricultural industries in recent years. Chiral compounds can have very different pharmacological 
activities in the biological system. The determination of these differences in the pharmacological 
activities will ultimately require a stereoselective analytical assay to evaluate the enantiomeric puri-
ty of chiral compounds.
Ethyl spiro[cyclopropane-1,3’-oxindole]-2-carboxylates 1 are possess a HIV-1 non-nucleoside 
reverse transcriptase inhibitors activity [1,2]. Stereo-isomeric nitriles 2 were prepared [3] and in-
vestigated in the hydrolysis resolution reactions for obtaining acids. 
N
H
O
Br
EtO
2
C
1
N
H
O
Br
H CO
2
H
N
H
O
Br
H CONH
2
N
H
O
Br
NC
2
+
3
4
NaOH/H
2
O
80
o
C, 36 h
The preliminary results from this study indicate that 4.5 mol aqueous solutions of NaOH at 
+80
o
C for 36 hours is suitable media for achieving stereo-isomeric pure spirocyclopropanes. Such 
condition gives pure cis -acid 3 and the trans-amide 4.
 
The author gratefully acknowledges funding though a grant from World Federation of Scien-
tists. 
 
1. Lopez-Alvarado P., Steinhoff J., Miranda S., Avendan C., Menendez Carlos J. Tetrahedron, 65, 
1660, 2009. 
2. Tao Jiang, Kelli L. Kuhen, Karen Wolff, Hong Yin, Kimberly Bieza, Jeremy Caldwell, Badry 
Bursulaya, Tom Yao-Hsing Wub, Yun He. Bioorganic & Medicinal Chemistry Letters, 16, 2105, 2006. 
3. Сукман Н.С., Бец Л.П., Шаргаровский В., Стынгач Е.П., Макаев Ф.З. VII Всероссийская на-
учная конференция «ХИМИЯ И МЕДИЦИНА, ОРХИМЕД-2009» с Молодежной научной школой. 
Уфа, Россия. 211, 2009. 

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