Home / Articles / Reactions of carbonyl compounds with α,β-unsaturated nitriles as a convenient pathway to carbo- and heterocycles

Reactions of carbonyl compounds with α,β-unsaturated nitriles as a convenient pathway to carbo- and heterocycles

Yulii Alekseevich Sharanin 1
Yulii Alekseevich Sharanin
, 
Mikhail Pavlovich Goncharenko 1
Mikhail Pavlovich Goncharenko
, 
Victor Petrovich Litvinov 2
Victor Petrovich Litvinov
1 Luhansk Taras Schevchenko State Pedagogical University
2 N. D. Zelinskii Institute of Organic Chemistry
Published 30 November 1997
Communication , Volume 67, Issue 5, 393-422
36
Share
Cite this
GOST
 | 
Cite this
GOST
Sharanin Y. A., Goncharenko M. P., Litvinov V. P. Reactions of carbonyl compounds with α,β-unsaturated nitriles as a convenient pathway to carbo- and heterocycles // Russian Chemical Reviews. 1998. Vol. 67. No. 5. pp. 393-422.
GOST all authors (up to 50)
Sharanin Y. A., Goncharenko M. P., Litvinov V. P. Reactions of carbonyl compounds with α,β-unsaturated nitriles as a convenient pathway to carbo- and heterocycles // Russian Chemical Reviews. 1998. Vol. 67. No. 5. pp. 393-422.
RIS
 | 
Cite this
RIS
TY - JOUR
DO - 10.1070/RC1998v067n05ABEH000371
UR - https://rcr.colab.ws/publications/10.1070/RC1998v067n05ABEH000371
TI - Reactions of carbonyl compounds with α,β-unsaturated nitriles as a convenient pathway to carbo- and heterocycles
T2 - Russian Chemical Reviews
AU - Sharanin, Yulii Alekseevich
AU - Goncharenko, Mikhail Pavlovich
AU - Litvinov, Victor Petrovich
PY - 1998
DA - 1997/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 393-422
IS - 5
VL - 67
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
@article{1998_Sharanin,
author = {Yulii Alekseevich Sharanin and Mikhail Pavlovich Goncharenko and Victor Petrovich Litvinov},
title = {Reactions of carbonyl compounds with α,β-unsaturated nitriles as a convenient pathway to carbo- and heterocycles},
journal = {Russian Chemical Reviews},
year = {1998},
volume = {67},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC1998v067n05ABEH000371},
number = {5},
pages = {393--422},
doi = {10.1070/RC1998v067n05ABEH000371}
}
MLA
Cite this
MLA
Sharanin, Yulii Alekseevich, et al. “Reactions of carbonyl compounds with α,β-unsaturated nitriles as a convenient pathway to carbo- and heterocycles.” Russian Chemical Reviews, vol. 67, no. 5, Nov. 1998, pp. 393-422. https://rcr.colab.ws/publications/10.1070/RC1998v067n05ABEH000371.
Views / Visits / Downloads
14 / 14 / 6

Abstract

Published data on the methods for synthesis of carbo- and heterocyclic compounds based on reactions of α,β-unsaturated nitriles with carbonyl compounds and activated phenols are surveyed. It is demonstrated that all these reactions occur via nucleophilic addition of the carbanion generated from a carbonyl compound to the double bond of an unsaturated nitrile (the Michael reaction). The main routes of transformation of the adducts into carbo- and heterocyclic compounds are considered. The methods for regioselective preparation of fused 4H-pyrans or 1,4-dihydropyridines by varying conditions of cyclisation of Michael adducts are discussed. The bibliography includes 249 references.

References

5.
5
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1953
6.
6
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
7.
7
E. Rabinowitch
"Photosynthesis" , 1956
8.
8
V. N. Kondrat'ev
"Kinetika Reaktsii v Gazovoi Faze" (Kinetics of Reactions in the Gas Phase) , 1959
9.
9
V. H. Lynch
Carnegie Inst. Year Book , 1954
11.
11
T. T. Bannister
Diss. Abstr. , 1959
12.
12
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
13.
13
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1954
17.
17
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1958
18.
18
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1951
19.
19
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1959
21.
Synthesis in the series of lycopodium alkaloids. VII. the synthesis of 12-epi-lycopodine
Dugas H., Hazenberg M.E., Valenta Z., Wiesner K.
Tetrahedron Letters , 1967
22.
1-Ethyl-1,4-dihydro-4-oxo-7-(pyridinyl)-3-quinolinecarboxylic acids. I. Synthesis of 3- and 4-(3-aminophenyl)pyridine intermediates
Carabateas P.M., Brundage R.P., Gelotte K.O., Gruett M.D., Lorenz R.R., Opalka C.J., Singh B., Thielking W.H., Williams G.L., Lesher G.Y.
Journal of Heterocyclic Chemistry , 1984
24.
24
M. S. Ashkinazi
Dokl. Akad. Nauk SSSR , 1951
25.
25
G. W. Robinson
J. Chem. Phys. , 1955
26.
26
B. Ya. Dain
1957
27.
27
A. A. Krasnovskii
Biofizika , 1956
28.
28
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1955
29.
31.
31
A. A. Krasnovskii
Biokhimiya , 1960
32.
Dimerisation of 3-aryl-2-cyanothioacrylamides. A [2s+ 4s] cyclo-addition to give substituted 3,4-dihydro-2H-thiopyrans
Brunskill J.S., De A., Ewing D.F.
Journal of the Chemical Society Perkin Transactions 1 , 1978
33.
33
M. B. Neiman
"Issledovanie Mekhanizma Okisleniya Butana" (Research on the Mechanism of the Oxidation of Butane) , 1939
34.
34
G. W. Robinson
J. Chem. Phys. , 1886
35.
35
Z. K. Maizus
Dokl. Akad. Nauk SSSR , 1960
36.
36
J. Billon
Bull. Soc. chim. France , 1960
37.
37
L. M. Kosobutskaya
Dokl. Akad. Nauk SSSR , 1950
38.
38
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1956
41.
THE INFRARED SPECTRA OF SOME CYCLIC MALONATES
Abramovitch R.A.
Canadian Journal of Chemistry , 1959
42.
42
L. K. Obukhova
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1960
43.
43
N. Bunge
Ber. Deutsch. Chem. Ges. , 1870
44.
Zur Chemie des 4-Phenyl-thiazoly-(2)-acetonitrils
Schäfer H., Gewald K.
Journal für praktische Chemie , 1974
45.
45
W. Hendrich
Roczniki Chemii , 1958
46.
46
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1955
47.
47
G. Oster
"Research in Photosynthesis" , 1957
48.
48
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1955
50.
50
G. Glacomello
Gazzetta. , 1935
51.
Chemistry of a-Cyanothioacetamide
A. Daboun H., Y. Riad B., M. Negm A., E. Abdou S.
Heterocycles , 1987
52.
52
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1957
53.
53
D. Porretand E. Rabinowitch
Nature , 1937
55.
55
G. A. Bogdanovskii
1958
56.
56
T. Iasui
Bull. Chem. Soc. Japan. , 1935
57.
57
R. Livingston
"Research in Photosynthesis" , 1957
58.
58
N. E. Khomutov
1953
60.
The Michael Condensation. II. The Reactivity of the Addendum1
Connor R., Andrews D.B.
Journal of the American Chemical Society , 1934
61.
61
A. N. Terenin
1959
62.
62
A. A. Krasnovskii
"Sbornik, Voprosy Khimicheskoi Kinetiki" (Symposium, Problems of Chemical Kinetics) , 1955
63.
63
1930
64.
Dicyanmethylenpyrazolinone und deren Bedeutung als Chromophor. Synthesen mit Nitrilen, 80. Mitt.
67.
Tieffarbige Pseudooxo-Krokonsäurebisamide
Junek H., Zuschnig G., Thierrichter R., Gfrerer G., Sterk H.
Monatshefte fur Chemie , 1982
71.
71
Yu. A. Shlyapnikov
Vysokomol. Soed. , 1962
72.
72
A. F. Lukovnikov
"Starenie i Stabilizatsiya Polimerov" (Aging arid Stabilisation of Polymers) , 1963
73.
73
T. Skwarski
Chem. Abs. , 1957
74.
74
F. F. Litvin
Uspekhi Fiz. Nauk , 1960
75.
Über das 4-Oxycumarin
Klosa J.
Archiv der Pharmazie , 1952
76.
76
A. N. Terenin
"Fotokhimiya Krasitelei" (The Photochemistry of Dyes) , 1947
77.
77
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
78.
78
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
80.
Über den wirkungsmechanismus des dicumarols und verwandter verbindungen
Martius C., Nitz-Litzow D.
Biochimica et Biophysica Acta - General Subjects , 1953
81.
Structure of (phenyl)bis(4-hydroxybenzo-2H-pyran-2-one-3-yl)methane
Valente E.J., Eggleston D.S.
Acta Crystallographica Section C Crystal Structure Communications , 1989
87.
Zayed S.E., Harb A.A., Elnagdi M.H.
Collection of Czechoslovak Chemical Communications , 2004
88.
88
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1946
89.
Synthesen mit nitrilen XXXI / Syntheses with nitriles, XXXI
Junek H., Aigner H.
Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences , 1970
91.
91
L. M. Vorob'eva
Biokhimiya , 1956
92.
92
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
94.
Synthetic Approaches to the 4H-Pyran Ring
L. Soto J., Seoane C., L. Soto J., Quinterio M.
Heterocycles , 1980
97.
Spiro heterocyclic compounds. III. Synthesis of spiro[oxindole-3,4'-(4'H-pyran)] compounds.
HIGASHIYAMA K., OTOMASU H.
Chemical and Pharmaceutical Bulletin , 2011
99.
99
V. V. Zolotarev
1938
100.
100
V. V. Zolotarev
Chem. Abs. , 1941
102.
102
F. Fichter
Helv. Chim. Acta , 1922
103.
103
L. N. Bell
Dokl. Akad. Nauk SSSR , 1956
104.
104
O. P. Osipova
Dokl. Akad. Nauk SSSR , 1950
105.
105
F. F. Litvin
Dokl. Akad. Nauk SSSR , 1958
106.
106
F. Fichter
Helv. Chim. Acta , 1927
107.
Marchalín Š., Pavlíková F., Ilavský D.
Collection of Czechoslovak Chemical Communications , 2010
108.
Synthese von 4H-Pyrano[2,3-d]pyrimidinen
Marchal�n ?., Ilavsk� D., Bruncko M.
Monatshefte fur Chemie , 1989
109.
Marchalín Š., Ilavský D., Kováč J., Bruncko M.
Collection of Czechoslovak Chemical Communications , 2010
110.
Activated nitriles in heterocyclic synthesis. The reaction of cinnamonitrile derivatives with active methylene reagents
112.
Studies on Heterocyclic Enamines: New Synthesis of Pyrano[2,3-b]pyndine, Pyrano[2,3-d]pyrimidine and Pyrano[2,3-c]pyrazole Derivatives
Abed N.M., Ibrahim N.S., Elnagdi M.H.
Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences , 1986
113.
Studies on heterocyclic enamines: New syntheses of 4H-pyranes, pyranopyrazoles and pyranopyrimidines
Elnagdi M.H., Abdel-Motaleb R.M., Mustafa M., Zayed M.F., Kamel E.M.
Journal of Heterocyclic Chemistry , 1987
114.
Activated Nitriles in Heterocyclic Synthesis: Novel Syntheses of Pyrano[2,3-b]pyridines and Pyrano[2,3-d]pyrimidines
Elgemeie G.E., El-Kerim A., Gohar M., Regaila H.A., Elfahham H.A.
Archiv der Pharmazie , 1988
115.
Development of methods for the synthesis of chiral, highly functionalized 2-amino-4-aryl-4H-pyrans
Marco J.L., Martín N., Martínez-Grau A., Seoane C., Albert A., Cano F.H.
Tetrahedron , 1994
117.
117
V. V. Levchenko
Zhur. Obshch. Khim. , 1948
118.
118
V. M. Rodionov
Zhur. Obshch. Khim. , 1935
119.
119
V. V. Levchenko
Zhur. Obshch. Khim. , 1947
120.
120
V. V. Levchenko
Zhur. Obshch. Khim. , 1948
121.
121
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1953
122.
122
S. R. Rafikov
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1953
123.
123
V. V. Levchenko
Zhur. Obshch. Khim. , 1952
124.
124
V. V. Levchenko
Zhur. Obshch. Khim. , 1952
126.
126
J. Wiemannand Ch. Clachet
Compt. rend. , 1948
127.
127
R. Pasternak
Helv. Chim. Acta , 1948
128.
A New Route to 4H-Pyrano[2,3-c]pyrazoles
Tacconi G., Gatti G., Desimoni G., Messori V.
Journal für praktische Chemie , 1980
129.
129
J. Wiemann
Bull. Soc. chim. France , 1955
130.
130
J. Wiemann
Bull. Soc. chim. France , 1958
131.
131
N. Thooi
Compt. rend. , 1958
133.
133
C. Wilson
Trans. Electrochem. Soc. , 1941
134.
134
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1948
135.
135
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1945
136.
136
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1954
137.
137
S. R. Rafikov
Zh. Obshch. Khim. , 1944
138.
138
S. Ono
J. Chem. Soc. Japan , 1957
139.
139
I. L. Knunyants
1959
140.
Synthesis of Condensed 4H-Pyrans: The reaction of 1,1-dimethyl-3,5-diketocyclohexane with cinnamonitriles
141.
141
Friedl.
142.
142
1913
143.
143
Friedl.
144.
144
1912
145.
145
Friedl.
146.
146
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1952
147.
CONDENSATION OF CERTAIN NITRILES AND VARIOUS POLY-HYDROXYPHENOLS TO FORM PHENOLIC ACIDS
Langley W.D., Adams R.
Journal of the American Chemical Society , 1922
148.
148
P. Kresse
Chem. Abs. , 1960
149.
Direct Synthesis of Dihydrocoumarin and Its Derivatives
Sato K., Amakasu T., Abe S.
Journal of Organic Chemistry , 1964
150.
150
Ya. E. Bernadskaya
"Iskusstvennoe Volokno" (Artificial Fibres) , 1952
151.
151
V. M. Rodionov
Zhur. Obshch. Khim. , 1936
152.
153.
153
1899
154.
154
Friedl.
155.
155
M. V. Mal'tsev
Izv. Vys. Ucheb. Zaved., Tsvet. Met. , 1960
158.
158
Friedl.
159.
Elagamey A.G., El-Taweel F.M., Sowellim S.Z., Sofan M.A., Elnagdi M.H.
Collection of Czechoslovak Chemical Communications , 2010
160.
160
1912
161.
161
Friedl.
162.
162
1917
163.
163
Friedl.
164.
164
1917
165.
165
Friedl.
166.
166
1917
167.
167
Friedl.
168.
168
1918
169.
Nitriles in Heterocyclic Synthesis: The Reaction of 2-Thiocarbamoyl Cinnamonitriles with Active Methylene Reagents
El-Torgoman A.M., El-Kousy S.M., Kandeel Z.E.
Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences , 1987
170.
170
1918
172.
172
1918
173.
Synthesis of 4-methylthio-2(1H)-pyridone derivatives using ketene dithioacetals
Tominaga Y., Kawabe M., Hosomi A.
Journal of Heterocyclic Chemistry , 1987
174.
174
S. Calvert
India Rubber Tire Rev. , 1926
175.
175
I. Mayer
1966
176.
176
G. V. Samsonov
"Metody Ispytaniya na Mikrotverdost' i Pribory" (Methods of Microhardness Testing and Apparatus) , 1965
177.
177
J. Henry
Proc. R. Irish Acad. , 1945
178.
178
1946
179.
ADVANCES IN THE CHEMISTRY OF 3-CYANOPYRIDIN-2(1H)-ONES, -THIONES, AND -SELENONES
Litvinov V.P., Rodinovskaya L.A., Sharanin Y.A., Shestopalov A.M., Senning A.
Sulfur Reports , 1992
183.
183
Chem. Abs. , 1947
186.
186
Chem. Abs. , 1956
187.
187
1954
191.
191
M. Matsui
Mem. Coll. Sci., Kyoto Univ. , 1920
192.
Zur Synthese von 4-Aryl-5,6-dihydro-benzo[h]chinolinen
Otto H., Rinus O., Schmelz H.
Monatshefte fur Chemie , 1979
195.
195
M. Allen
J. Chem. Soc. , 1961
196.
Heterocyclen aus Enaminonen
Möhrle H., Novak H.
Archiv der Pharmazie , 1982
197.
Reaction of 6-aminouracils with ketenethioacetals.
TOMINAGA Y., KOHRA S., OKUDA H., USHIROGOCHI A., MATSUDA Y., KOBAYASHI G.
Chemical and Pharmaceutical Bulletin , 2011
198.
198
W. Cohen
Rec. Trav. chim. , 1919
199.
199
Yu. K. Delimarskii
Byull. Izobr. , 1970
200.
Studies on conjugated nitriles. V. Reaction of 3-benzoyl- and 3-ethoxycarbonylacrylonitriles with enamines.
AKIYAMA Y., ABE J., TAKANO T., KAWASAKI T., SAKAMOTO M.
Chemical and Pharmaceutical Bulletin , 2011
203.
Arylidenemalononitriles in heterocyclic syntheses: a novel synthesis of pyrido[2,3-d]pyrimidines
Gogoi M., Bhuyan P., Sandhu J.S., Baruah J.N.
Journal of the Chemical Society Chemical Communications , 1984
204.
204
Cherkesov A I
Ref. Zh. Khim. , 1968
205.
Synthesis of heterocyclic compounds. Part 46. The reactions of malonamide and 2-cyanoacetamide with substituted propenones
Soto J.L., Seoane C., Zamorano P., Rubio M.J., Monforte A., Quinteiro M.
Journal of the Chemical Society Perkin Transactions 1 , 1985
206.
Reactions with α-substituted cinnamonitriles. A novel synthesis of hexa-substituted pyridines
Hammouda H.A., Ahmed, El-Reedy M., Hussain S.M.
Journal of Heterocyclic Chemistry , 1986
208.
208
O. A. Reutov
"Teoreticheskie Problemy Organicheskoi Khimii" (Theoretical Problems in Organic Chemistry) , 1956
209.
209
C. J. Haggerty
Trans. Am. Electrochem. Soc. , 1929
210.
210
H. L. Wheeler
Chem. Zentr. , 1908
211.
211
C. Schall
Z. Elektrochem. , 1923
212.
212
L. V. Pavlova
Zh. Obshch. Khim. , 1965
213.
213
F. Yu. Rachinskii
"Khimiya Seraorganicheskikh Soedinenii, Soderzhashchikh-sya v Neftyakh i Nefteproduktakh" (Chemistry of Organo-sulphur Compounds Present in Petroleum and Petroleum Products) , 1966
214.
214
L. V. Pavlova
1965
216.
216
A. P. Tomilov
Zhur. Prikl. Khim. , 1959
217.
217
1925
218.
218
Chem. Zentr. II , 1925
219.
219
G. I. Pustoshkin
Collected Papers "Biologicheskie Aktivnie Soedinenii" (Biologically Active Compounds) , 1955
220.
220
K. Ziegler
Angew. Chem. , 1955
222.
222
Chem. Abs. , 1961
223.
SYNTHESIS AND BIOLOGICAL ACTIVITY OF SOME NEW HETEROCYCLIC QUINOLINE DERIVATIVES
Awad I.M., Abdel-rahman A.E., Bakhite E.A.
Phosphorus, Sulfur and Silicon and the Related Elements , 1991
224.
224
Chem. Abs. , 1959
225.
225
1960
226.
226
Chem. Abs. , 1961
227.
227
B. Roetheke
1958
228.
228
B. Roetheke
Chem. Abs. , 1959
229.
229
1959
230.
230
Chem. Abs. , 1962
231.
231
1960
232.
232
Chem. Abs. , 1960
233.
233
P. Cotter
J. Am. Chem. Soc. , 1956
234.
234
Ebach E A
Chem. Abs. , 1966
235.
235
R. Peffen
1967
236.
236
P. Peshev
Rev. internat. hautes Temperat. et Réfract. , 1969
237.
237
P. Peshev
Rev. internat. hautes Temperat. et Réfract. , 1969
238.
238
Brown G P
Am. Chem. Soc., Polymer Preprints , 1964
239.
239
Mendelbaum H. G.
Bull. Soc. chim. France , 1973
240.
240
W. A. Waters
"The Chemistry of Free Radicals" , 1948
241.
241
M. S. Kharasch
"Grignard Reactions of Nonmetallic Substances" , 1954
242.
242
N. N. Seroenov
"O Nekotorykh Problemakh Khimicheskoi Kinetiki i Reaktsionnoi Sposobnosti" (Some Problems in Chemical Kinetics and Reactivity) , 1958
243.
Structure of morpholinium 5-acetyl-3-cyano-1,4-dihydro-6-methyl-4-(2-nitrophenyl)-2-pyridinethiolate, C4H10NO+.C15H12N3O3S−
Nesterov V.N., Shklover V.E., Struchkov Y.T., Sharanin Y.A., Shestopalov A.M., Rodinosvskaya L.A.
Acta Crystallographica Section C Crystal Structure Communications , 1985
244.
244
C. Wilson
Record. Chem. Prog. , 1949
245.
245
G. A. Meerson
1958
246.
α,β-Unsaturated Nitriles in Heterocyclic Synthesis. Novel Synthesis of Pyridines and Thieno[2,3-b]pyridine Derivatives
247.
247
E. I. Levkoeva
Khim. Geterotsikl. Soed. , 1976
248.
248
M. Ya. Fioshin
Plasticheskie Massy , 1960
249.
249
A. I. Fedorova
Dokl. Akad. Nauk SSSR , 1961
250.
250
D. Goerrig
1955
251.
251
D. Goerrig
Chem. Abs. , 1959
252.
252
D. Goerrig
1956
253.
253
D. Goerrig
Chem. Abs. , 1959
254.
254
M. G. Safarov
1975
255.
255
Tomita M
Chem. Abs. , 1939
256.
256
Z. V. Zvonkova
Zh. Strukt. Khim. , 1977
257.
257
L. Ya. Markovskii
Zh. Neorg. Khim. , 1957
258.
258
P. P. Alexander
Metals Alloys , 1938
259.
259
V. Elyutin
Trudy Moskov. Inst. Stali , 1939
260.
260
C. Friedel
Compt. rend. , 1876
261.
261
C. Friedel
Ann. Chim. Phys. , 1876
262.
262
C. Friedel
Ann. Chim. Phys. , 1876
263.
263
R. E. Spivak
Azerb. Neft. Khoz. , 1975
264.
264
E. Friederich
1922
265.
265
E. A. Ostroumov
Zavod. Lab. , 1935
266.
266
N. G. Mudrik
1975