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Adamantane derivatives containing heterocyclic substituents in the bridgehead positions. Synthesis and properties

Mai-Genrikh Avgustovich Shvekhgeimer 1
Mai-Genrikh Avgustovich Shvekhgeimer
1 Moscow State Textile Academy named after A. N. Kosygin
Published 30 November 1995
Communication , Volume 65, Issue 7, 555-598
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Shvekhgeimer M. A. Adamantane derivatives containing heterocyclic substituents in the bridgehead positions. Synthesis and properties // Russian Chemical Reviews. 1996. Vol. 65. No. 7. pp. 555-598.
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Shvekhgeimer M. A. Adamantane derivatives containing heterocyclic substituents in the bridgehead positions. Synthesis and properties // Russian Chemical Reviews. 1996. Vol. 65. No. 7. pp. 555-598.
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TY - JOUR
DO - 10.1070/RC1996v065n07ABEH000272
UR - https://rcr.colab.ws/publications/10.1070/RC1996v065n07ABEH000272
TI - Adamantane derivatives containing heterocyclic substituents in the bridgehead positions. Synthesis and properties
T2 - Russian Chemical Reviews
AU - Shvekhgeimer, Mai-Genrikh Avgustovich
PY - 1996
DA - 1995/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 555-598
IS - 7
VL - 65
ER -
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@article{1996_Shvekhgeimer,
author = {Mai-Genrikh Avgustovich Shvekhgeimer},
title = {Adamantane derivatives containing heterocyclic substituents in the bridgehead positions. Synthesis and properties},
journal = {Russian Chemical Reviews},
year = {1996},
volume = {65},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC1996v065n07ABEH000272},
number = {7},
pages = {555--598},
doi = {10.1070/RC1996v065n07ABEH000272}
}
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Shvekhgeimer, Mai-Genrikh Avgustovich. “Adamantane derivatives containing heterocyclic substituents in the bridgehead positions. Synthesis and properties.” Russian Chemical Reviews, vol. 65, no. 7, Nov. 1996, pp. 555-598. https://rcr.colab.ws/publications/10.1070/RC1996v065n07ABEH000272.
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Abstract

Data on the synthesis, transformations, and applications of adamantane derivatives containing heterocyclic substituents in the bridgehead positions are surveyed, described systematically, and analysed.The bibliography includes 202 references.

References

1.
1
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
2.
2
A. A. Krasnovskii
Zhur. Fiz. Khim. , 1956
3.
3
M. F. Shostakovskii
"Prostye Vinilovye Efiry" (Vinyl Ethers) , 1952
6.
6
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
7.
Advances in the Chemistry of Adamantane
Sevost'yanova V.V., Krayushkin M.M., Yurchenko A.G.
Russian Chemical Reviews , 1970
8.
9
V. H. Lynch
Carnegie Inst. Year Book , 1954
9.
Polymeric Derivatives of Adamantane
Khardin A.P., Radchenko S.S.
Russian Chemical Reviews , 1982
10.
Unsaturated Adamantane Derivatives
Bagrii E.I., Saginaev A.T.
Russian Chemical Reviews , 1983
11.
14
V. B. Evstigneev
Zhur. Fiz. Khim. , 1958
12.
15
A. S. Holt
"Research in Photosynthesis" , 1957
13.
16
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
14.
17
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1958
15.
18
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1951
16.
19
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1959
17.
Synthese und Struktur adamantylsubstituierter Methylenaziridine 1)
Quast H., Jakob R., Peters K., Peters E., Schnering H.G.
Chemische Berichte , 1984
18.
Synthesis of New Aziridime-Carboxamide-, Thioamide-, Amidime-Derivatives and Their Reaction With Phosgene
Lambert C., Merényi R., Caillaux B., Viehe H.G.
Bulletin des Sociétés Chimiques Belges , 2010
19.
A stable α-lactarn derived from adamantane
Talaty E.R., Dupuy A.E., Cancienne A.E.
Journal of Heterocyclic Chemistry , 1967
21.
Aziridinone derived from 1-aminoadamantane
Talaty E.R., Dupuy A.E.
Journal of Medicinal Chemistry , 1969
22.
Ferrocene studies. V. Potential medicinal agents
Popp F.D., Moynahan E.B.
Journal of Medicinal Chemistry , 1970
28.
31
A. A. Krasnovskii
Biokhimiya , 1960
29.
Reactions of α-lactams with t-butyl-lithium
Talaty E.R., Utermoehlen C.M.
Journal of the Chemical Society Chemical Communications , 1974
30.
33
M. B. Neiman
"Issledovanie Mekhanizma Okisleniya Butana" (Research on the Mechanism of the Oxidation of Butane) , 1939
31.
34
G. W. Robinson
J. Chem. Phys. , 1886
32.
35
Z. K. Maizus
Dokl. Akad. Nauk SSSR , 1960
33.
36
J. Billon
Bull. Soc. chim. France , 1960
34.
37
L. M. Kosobutskaya
Dokl. Akad. Nauk SSSR , 1950
35.
New investigations of the reaction of epichlorohydrin with hindered amines: X-ray and NMR analyses
Laguerre M., Boyer C., Leger J., Carpy A.
Canadian Journal of Chemistry , 1989
37.
40
A. A. Krasnovskii
Biofizika , 1960
38.
41
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1950
41.
Microbiological oxygenation of acylated 1-adamantanamines. Stereochemistry and structural determinations
Herr M.E., Johnson R.A., Murray H.C., Reineke L.M., Fonken G.S.
Journal of Organic Chemistry , 1968
42.
45
W. Hendrich
Roczniki Chemii , 1958
43.
46
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1955
44.
47
G. Oster
"Research in Photosynthesis" , 1957
45.
48
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1955
46.
49
A. A. Krasnovskii
Biofizika , 1958
48.
51
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1954
49.
52
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1957
50.
53
D. Porretand E. Rabinowitch
Nature , 1937
51.
54
R. Livingston
J. Phys. Chem. , 1941
53.
56
T. Iasui
Bull. Chem. Soc. Japan. , 1935
54.
57
R. Livingston
"Research in Photosynthesis" , 1957
55.
58
N. E. Khomutov
1953
57.
60
A. N. Terenin
Optika i Spektrosk. , 1956
58.
Adamantylation of N-Unsubstituted Pyrazole Derivatives: Mechanistic and Structural Studies
Mar誕 Claramunt R., Cabildo P., Forfar I., Foces-Foces C., L. Liamas-Saiz A., Elguero J.
Heterocycles , 1994
59.
62
A. A. Krasnovskii
"Sbornik, Voprosy Khimicheskoi Kinetiki" (Symposium, Problems of Chemical Kinetics) , 1955
60.
63
1930
61.
Regioselective adamantylation of N-unsubstituted pyrazole derivatives
Cabildo P., Claramunt R.M., Forfar I., Elguero J.
Tetrahedron Letters , 1994
62.
65
A. A. Krasnovskii
Biofizika , 1959
63.
66
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
64.
67
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1940
65.
Syntheses and Biological Activities of 2-(Adamantylmethyl)benzimidazoles and -imidazolines
Kuźmierkiewicz W., S??czewski F., Foks H., Kaliszan R., Damasiewicz B., Nasal A., Radwańska A.
Archiv der Pharmazie , 1986
66.
69
B. Commoner
1958
67.
Synthesis of Adamantane Derivatives. III. Synthesis of Adamantane Heterocycles
Sasaki T., Eguchi S., Toru T.
Bulletin of the Chemical Society of Japan , 1969
68.
Synthesis and reactivity of new l-(1-adamantyl)pyrazoles
Cabildo P., Claramunt R.M., Elguero J.
Journal of Heterocyclic Chemistry , 1984
69.
Adamantylazoles.5. The molecular structure of 1-(1-adamantyl)pyrazoles
Cabildo P., Claramunt R.M., Sanz D., Foces-Foces M.C., Cano F.H., Fayet J.P., Vertut M.C., Elguero J.
Journal of Heterocyclic Chemistry , 1986
70.
Metal complexes in organic synthesis—V
Gonzalez A., Marquet J., Moreno-Mañas M.
Tetrahedron , 1986
71.
74
F. F. Litvin
Uspekhi Fiz. Nauk , 1960
72.
75
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
73.
76
A. N. Terenin
"Fotokhimiya Krasitelei" (The Photochemistry of Dyes) , 1947
74.
[Adamantyl-(1)]-imidazole
Schubert H., Born H.
Zeitschrift für Chemie , 2010
75.
Pyrolysis of 1-adamantyl azidomethyl ketone
Sternbach L.H., Ning R.Y.
Journal of Medicinal Chemistry , 1970
76.
79
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1952
77.
80
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1937
78.
81
J. C. Ghosh
J. Indian Chem. Soc. , 1934
79.
82
G. P. Brin
Biokhimiya , 1957
80.
83
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
81.
Imidazo[5,1-a]isochinoline
Zimmer H., Glasgow D.G., McClanahan M., Novinson T.
Tetrahedron Letters , 1968
82.
85
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
83.
86
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1958
84.
87
J. F. Arens
"Advances in Organic Chemistry" , 1960
85.
88
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1946
86.
89
A. A. Krasnovskii
Izd. Akad. Nauk SSSR, Moscow , 1955
89.
92
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
90.
93
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1956
91.
A stable crystalline carbene
Arduengo A.J., Harlow R.L., Kline M.
Journal of the American Chemical Society , 1991
93.
96
L. M. Vorob'eva
Biokhimiya , 1958
94.
97
A. N. Terenin
Dokl. Akad. Nauk SSSR , 1952
96.
99
V. V. Zolotarev
1938
97.
100
V. V. Zolotarev
Chem. Abs. , 1941
98.
101
M. F. Shostakovskii
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1960
99.
102
F. Fichter
Helv. Chim. Acta , 1922
100.
103
L. N. Bell
Dokl. Akad. Nauk SSSR , 1956
101.
Synthesis of 5-substituted 1-(1-adamantyl) tetrazoles and related compounds
Kevill D.N., Weitl F.L.
Journal of Organic Chemistry , 1970
102.
105
F. F. Litvin
Dokl. Akad. Nauk SSSR , 1958
103.
106
F. Fichter
Helv. Chim. Acta , 1927
104.
107
M. F. Shostakovskii
Zhur. Obshch. Khim. , 1961
105.
108
F. Fichter
Helv. Chim. Acta , 1924
106.
109
F. Ficher
Bull. Soc. chim. France (4) , 1916
107.
110
M. F. Shostakovskii
Dokl. Akad. Nauk SSSR , 1960
108.
111
M. Calvin
1956
109.
Functionalization of saturated hydrocarbons. 14. Further studies on the mechanism of Gif-type systems
Barton D.H., Halley F., Ozbalik N., Schmitt M., Young E., Balavoine G.
Journal of the American Chemical Society , 1989
110.
113
H. Blum
"Photodynamic Action and Diseases caused Light" , 1940
111.
114
L. Segal
"Chemical Reactions of Polymers" , 1964
112.
115
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1957
113.
116
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1957
114.
117
V. V. Levchenko
Zhur. Obshch. Khim. , 1948
115.
118
V. M. Rodionov
Zhur. Obshch. Khim. , 1935
116.
119
V. V. Levchenko
Zhur. Obshch. Khim. , 1947
117.
120
V. V. Levchenko
Zhur. Obshch. Khim. , 1948
118.
121
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1953
119.
Displacement of the acyl group by alkyl radicals. A novel S R reaction of nitrogen-containing heteroaromatic compounds
Fiorentino M., Testaferri L., Tiecco M., Troisi L.
Journal of the Chemical Society Chemical Communications , 1976
120.
Structural effects on the reactivity of carbon radicals in homolytic aromatic substitution. Part 4. The nucleophilicity of bridgehead radicals
Fiorentino M., Testaferri L., Tiecco M., Troisi L.
Journal of the Chemical Society Perkin Transactions 2 , 1977
121.
124
V. V. Levchenko
Zhur. Obshch. Khim. , 1952
122.
125
K. A. Andrianov
Vysokomol. Soed. , 1960
123.
126
J. Wiemannand Ch. Clachet
Compt. rend. , 1948
124.
3-(Dialkylamino)methyladamantane-1-carboxylic acids
Kontonassios D., Sandris C., Tsatsas G., Casadio S., Lumachi B., Turba C.
Journal of Medicinal Chemistry , 1969
125.
128
J. Wiemann
Bull. Soc. chim. France , 1952
126.
129
J. Wiemann
Bull. Soc. chim. France , 1955
127.
Aromatic Vs diene reactivity of 2(1H)-pyridinone and its derivatives
Yadla R., Rehman H., Rao J.M., Mahesh V.K.
Tetrahedron , 1989
128.
131
N. Thooi
Compt. rend. , 1958
129.
132
G. Shima
Kyoto Univ. , 1929
130.
133
C. Wilson
Trans. Electrochem. Soc. , 1941
131.
134
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1948
132.
135
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1945
133.
136
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1954
134.
137
S. R. Rafikov
Zh. Obshch. Khim. , 1944
135.
138
S. Ono
J. Chem. Soc. Japan , 1957
136.
139
I. L. Knunyants
1959
137.
140
1912
138.
141
Friedl.
139.
142
1913
140.
143
Friedl.
141.
144
1912
142.
145
Friedl.
143.
146
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1952
144.
147
Y. Sasada
Acta Cryst. , 1898
145.
148
P. Kresse
Chem. Abs. , 1960
146.
Use of 2-oxazolidinones as latent aziridine equivalents. III. Preparation of N-substituted piperazines
Poindexter G.S., Bruce M.A., LeBoulluec K.L., Monkovic I.
Tetrahedron Letters , 1994
148.
3,4-Dihydro-2(1H)-quinazolinones
Coyne W.E., Cusic J.W.
Journal of Medicinal Chemistry , 1968
149.
152
W. Albert
Trans. Electrochem. Soc. , 1943
150.
Kuchař M., Štrof J., Vachek J.
Collection of Czechoslovak Chemical Communications , 2012
151.
Synthesis and biological activity of some 5-(1-adamantyl)pyrimidines. 2
Jonak J.P., Zakrzewski S.F., Mead L.H.
Journal of Medicinal Chemistry , 1971
152.
Synthesis and biological activity of some 5-substituted 2,4-diamino-6-alkylpyrimidines. 3
Jonak J.P., Zakrzewski S.F., Mead L.H.
Journal of Medicinal Chemistry , 1972
153.
156
J. S. Fruton
J. Biol. Med. , 1950
154.
157
1903
155.
158
Friedl.
156.
159
J. Tafel
Z. Elektrochem. , 1911
157.
160
1912
158.
161
Friedl.
159.
162
1917
160.
163
Friedl.
161.
Chemi- and bio-luminescent properties of coelenterazine analogues possessing an adamantyl group
Hirano T., Negishi R., Yamaguchi M., Chen F.Q., Ohmiya Y., Tsuji F.I., Ohashi M.
Journal of the Chemical Society Chemical Communications , 1995
162.
Adamantane and protoadamantanealkanamines as potential anti-Parkinson agents. 10
Chakrabarti J.K., Hotten T.M., Sutton S., Tupper D.E.
Journal of Medicinal Chemistry , 1976
163.
166
1917
164.
Potentiell virushemmende N-[adamantyl-(1)]-carbonsäureamide
Kreutzberger A., Schröders H.
Tetrahedron Letters , 1970
166.
169
Friedl.
167.
170
1918
168.
171
Friedl.
169.
172
1918
170.
173
Friedl.
171.
174
S. Calvert
India Rubber Tire Rev. , 1926
172.
175
I. Mayer
1966
173.
176
G. V. Samsonov
"Metody Ispytaniya na Mikrotverdost' i Pribory" (Methods of Microhardness Testing and Apparatus) , 1965
174.
Kuchař M.
Collection of Czechoslovak Chemical Communications , 2013
175.
Kuchař M., Kakáč B.
Collection of Czechoslovak Chemical Communications , 2012
177.
180
1946
178.
181
Chem. Abs. , 1947
179.
182
1947
180.
183
Chem. Abs. , 1947
181.
Factors controlling the fate of radical ipso intermediates. Homolytic alkylation of furan derivatives
Cogolli P., Testaferri L., Tiecco M., Tingoli M.
Journal of the Chemical Society Chemical Communications , 1979
183.
(Z)- and (E)-1,2-di(1-adamantyl)ethene
Marchand A.P., Xing D., Bott S.G., Ogawa K., Harada J.
Tetrahedron Letters , 1994
184.
187
1954
185.
188
Chem. Abs. , 1955
186.
189
M. Godchot
Bull. Soc. chim. France (5) , 1913
188.
191
M. Matsui
Mem. Coll. Sci., Kyoto Univ. , 1920
189.
The synthesis of 1- and 2-alkyladamantanes
Hoek W., Strating J., Wynberg H.
Recueil des Travaux Chimiques des Pays-Bas , 2010
190.
The synthesis of ω-functionalized 1-adamantylalkanes
Hoek W., Wynberg H., Strating J.
Recueil des Travaux Chimiques des Pays-Bas , 2010
191.
Synthesis of 3-aryl-1-adamantanemethylamines
Handa I., Bauer L.
Journal of Chemical & Engineering Data , 1984
192.
195
M. Allen
J. Chem. Soc. , 1961
193.
Factors controlling the selectivity of ipso-attack in homolytic aromatic substitutions. Reactions of alkyl radicals with nitrothiophen derivatives
Cogolli P., Maiolo F., Testaferri L., Tiecco M., Tingoli M.
Journal of the Chemical Society Perkin Transactions 2 , 1980
194.
197
J. Sicher
Chem. Listy , 1955
195.
198
W. Cohen
Rec. Trav. chim. , 1919
196.
199
Yu. K. Delimarskii
Byull. Izobr. , 1970
198.
Synthesis and X‐Ray Structures of New Macrocyclic Thioethers
Mlinarić‐Majerski K., Pavlović D., Luić M., Kojić‐Prodić B.
Chemische Berichte , 1994
199.
202
G. Shiroa
Mem. Coll. Sci., Kyoto Univ. , 1930
200.
203
L. Andrieux
Compt. rend. , 1929
201.
Synthesis and reactivity of adamantane-1-carbonitrile N-oxide
Dondoni A., Barbaro G., Battaglia A., Giorgianni P.
Journal of Organic Chemistry , 1972
202.
205
N. Bunge
Zhur. Russ. Fiz.-Khim. Obshch. , 1889
203.
206
J. Petersen
Z. Phys. Chem. , 1900
205.
208
O. A. Reutov
"Teoreticheskie Problemy Organicheskoi Khimii" (Theoretical Problems in Organic Chemistry) , 1956
206.
209
C. J. Haggerty
Trans. Am. Electrochem. Soc. , 1929
208.
Synthesis of adamantane derivatives—VII
Sasaki T., Eguchi S., Toru T.
Tetrahedron , 1969
209.
212
L. V. Pavlova
Zh. Obshch. Khim. , 1965
210.
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
211.
214
L. V. Pavlova
1965
212.
215
N. D. Tomashov
Zh. Prikl. Khim. , 1970
213.
1-Hydrazinoadamantan
Daeniker H.U.
Helvetica Chimica Acta , 1967
215.
218
Chem. Zentr. II , 1925
216.
219
G. I. Pustoshkin
Collected Papers "Biologicheskie Aktivnie Soedinenii" (Biologically Active Compounds) , 1955
217.
220
K. Ziegler
Angew. Chem. , 1955
218.
221
1960
219.
222
Chem. Abs. , 1961
220.
223
1959
221.
224
Chem. Abs. , 1959
223.
226
Chem. Abs. , 1961
224.
227
B. Roetheke
1958
225.
228
B. Roetheke
Chem. Abs. , 1959
226.
Homolytic aromatic ipso substitutions in benzothiazoles by the nucleophilic 1-adamantyl radical
Fiorentino M., Testaferri L., Tiecco M., Troisi L.
Journal of the Chemical Society Chemical Communications , 1977
227.
Displacement of the acyl group in benzothiazoles by nucleophilic alkyl radicals. Homolytic aromatic ipso-substitution
Fiorentino M., Testaferri L., Tiecco M., Troisi L.
Journal of the Chemical Society Perkin Transactions 2 , 1977
228.
Radical alkyldenitration. A synthetically useful example of homolytic aromatic Ipso-substitution reactions
Testaferri L., Tiecco M., Tingoli M., Fiorentino M., Troisi L.
Journal of the Chemical Society Chemical Communications , 1978
229.
Reaction of 1-formyladamantane with heterocyclic compounds. Mass spectra, antibacterial and antifungal activity
Fenech G., Monforte P., Chimirri A., Grasso S.
Journal of Heterocyclic Chemistry , 1979
230.
233
P. Cotter
J. Am. Chem. Soc. , 1956
231.
234
Ebach E A
Chem. Abs. , 1966
232.
235
R. Peffen
1967
234.
237
P. Peshev
Rev. internat. hautes Temperat. et Réfract. , 1969
235.
238
Brown G P
Am. Chem. Soc., Polymer Preprints , 1964
237.
240
W. A. Waters
"The Chemistry of Free Radicals" , 1948
238.
241
M. S. Kharasch
"Grignard Reactions of Nonmetallic Substances" , 1954
239.
242
N. N. Seroenov
"O Nekotorykh Problemakh Khimicheskoi Kinetiki i Reaktsionnoi Sposobnosti" (Some Problems in Chemical Kinetics and Reactivity) , 1958