Abstract
Research dealing with methods for the synthesis of 1,3-oxazacycloalkanes and their structures and homolytic and heterolytic transformations is reviewed.
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Literature cited
E. D., Bergmann, Chem. Rev., 53, 309 (1953).
Z. Eckstein and T. Urbanski, Adv. Heterocycl. Chem., 23, 1 (1978).
L. Knorr and H. Matthes, Ber., 34, 3484 (1901).
M. Kohn, Monatsh. Chem., 25, 817 (1904).
P. A. Laurent, Bull. Soc. Chim. France, No. 2, 571 (1967).
E. D. Bergmann and H. J. Resnich, J. Chem. Soc., No. 6, 1662 (1956).
G. Hambermehl, Chem. Ber., 96, 2029 (1963).
J. Fernander, S. A. Terol, J. Robbe, J. Chapat, R. Granger, L. Andrien, M. Fatome, and H. Sentenac-Roumanou, Trav. Soc. Pharm. Montpellier, 38, 147 (1978).
S. R. Tulyaganov and S. A. Khasanov, Uzb. Khim. Zh., 10, 32 (1966).
S. R. Tulyaganov, A. V., Yakubov, and A. Sultankulov, Uzb. Khim. Zh., 14, 45 (1970).
P. A. Layrent and P. D. Ferreirade Almeida, Bull. Soc. Chim. France, No. 2, 570 (1967).
S. A. Soliman, H. Abdine, and S. El-Nenaey, Aust. J. Chem., 28, 49 (1975).
S. A. Soliman, Can. J. Pharm. Sci., 8, 132 (1973).
L. Neelakatan, J. Org. Chem., 36, 2256 (1971).
A. H. Beckett and G. R. Jones, Tetrahedron, 33, 3313 (1977).
I. P. Boiko, Yu. F. Malina, O. I. Zhuk, Yu. Yu. Samitov, and B. V. Unkovskii, Zh. Org. Khim., 12, 80 (1976).
Yu. E. Kazantsev, Master's Dissertation, Moscow (1970).
I. P. Boiko, O. I. Zhuk, Yu. F. Malina, Yu. Yu. Samitov, and B. V. Unkovskii, Zh. Org. Khim., 12, 2107 (1976).
F. N. Latypova, Yu. F. Malina, and B. V. Unkovskii, in: The Chemistry and Technology of Organic Derivatives, Vol. 9, No. 2, Moscow Institute of Chemical Machinery-M. V. Lomonosov Moscow Institute of Fine Chemical Technology (1979), p. 3.
F. A. Alimirzoev, A. U. Stepanyants, F. N. Latypova, and B. V. Unkovskii, Deposited in ONIITEKhim, Cherkassy, 3084/79; Ref. Zh. Khim., Izh105 (1980).
I. P. Boiko, Yu. E. Kazantsev, Yu. F. Malina, O. I. Zhuk, Yu. Yu. Samitov, and B. V. Unkovskii, Khim. Geterotsikl. Soedin., No. 4, 467 (1973).
Yu. E. Kazantsev, I. P. Boiko, Yu. F. Malina, O. I. Zhuk, Yu. Yu. Samitov, and B. V. Unkovskii, Zh. Org. Khim., 9, 2597 (1973).
F. A. Alimirzoev, A. U. Stepanyants, F. N. Latypova, and B. V. Unkovskii, Deposited in ONIITEKhim, Cherkassy, No. 3093/79; Ref. Zh. Khim., 3B325 (1980).
G. Drefahl and H. H. Hörlhold, Chem. Ber., 94, 1657 (1961).
Z. Eckstein, P. Gluzinski, W. Hofman, and T. Urbanski, J. Chem. Soc., No. 2, 489 (1961).
A. F. McDonagh and H. E. Smith, J. Org. Chem., 33, 1 (1968).
M. E. Rennekamp, J. V. Paukstelis, and R. G. Cooks Tetrahedron, 27, 4407 (1971).
Zen-inchi Horii and Tareshi Inoi, Chem. Pharm. Bull., 13, 1151 (1965).
P. A. Laurent, Compt. Rend., 261, 1323 (1965).
A. N. Gafarov, L. N. Punegova, E. I. Loginova, S. S. Novikov, and N. K. Titov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 2189 (1978).
W. H. Watanabe and L. E. Conlon, J. Am. Chem. Soc., 79, 2825 (1957).
Zh. Seitkasymov and S. R. Tulyaganov, Deposited Paper No. 13543/71; Ref. Zh. Khim., 9Zh43 (1972).
A. Le Rouzic and M. Kerfanto, C. R. Acad. Sci., C, 279, 531 (1973).
M. Senkus, U.S. Patent No. 2447822; Chem. Abstr., 43, 1068 (1949).
Z. Eckstein, P. Gluzinski, and T. Urbanski, Bull. Acad. Pol. Sci., Ser. Sci. Chim., 12, 623 (1964).
Z. Eckstein, P. Gluzinski, E. Grochowski, M. Mordarski, and T. Urbanski, Bull. Acad. Pol. Sci. Sci. Chim., 10, 331 (1962).
H. D. Hartough, U.S. Patent No. 2647117; Chem. Abstr., 48, 8265 (1954).
H. D. Hartough, U.S. Patent No. 2647118; Chem. Abstr., 48, 7645 (1954).
K. J. Schmidle and R. C. Mansfield, J. Am. Chem. Soc., 77, 5698 (1955).
K. J. Schmidle and R. C. Mansfield, J. Am. Chem. Soc., 78, 425 (1956).
R. Quelet and A. M. Tourin, Ann. Chim., 11, 107 (1966).
J. B. Doughty, C. L. Lazzell, and A. R. Collet, J. Am. Chem. Soc., 72, 2866 (1950).
R. Oda, M. Okano, S. Tokiura, and A. Miyasu, Bull. Chem. Soc. Jpn., 35, 1216 (1962).
A. I. Meyers, A. Nabeja, H. W. Adiches, I. R. Poletzer, G. R. Malone, A. C. Kovelevsky, R. L. Wolen, and R. C. Portnow, J. Org. Chem., 38, 36 (1973).
A. I. Meyers and A. Nabeja, Chem. Commun., No. 22, 1163 (1967).
A. A. Baum and L. A. Karinsky, J. Am. Chem. Soc., 95, 3072 (1973).
M. J. Cook, R. A. Y. Jones, A. R. Katritzky, M. N. Manas, A. C. Richards, A. J. Sparrow, and D. L. Trepanier, J. Chem. Soc., Perkin Trans. 2, No. 4, 325 (1973).
A. R. Katritzky, R. A. Y. Jones, and D. L. Trepanier, J. Chem. Soc., B, No. 7, 1300 (1971).
R. A. Y. Jones, A. R. Katritzky, A. C. Richards, S. Saba, A. J. Sparrow, D. L. Trepaniers, Chem. Commun., No. 11, 673 (1972).
T. Urbanski, D. Gurne, R. Kolinski, H. Piotrowska, A. Jonczyc, B. Serafin, M. Szretter-Szmid, and M. Witanowski, Nitro Compounds, Proceedings of the International Symposium, Warsaw, p. 195 (published 1964); Chem. Abstr., 63, 16186 (1965).
T. Urbanski, Zh. Vses. Khim. Ova., 7, 396 (1962).
R. C. Cookson and T. A. Crabb, Tetrahedron, 24, 2385 (1968).
Y. Allingham, R. S. Cookson, T. A. Crabb, and S. Vary, Tetrahedron, 24, 4626 (1968).
F. G. Riddell and J. H. Lehn, J. Chem. Soc., B, No. 10, 1224 (1968).
M. Anteunis, G. Swaelens, and J. Gelan, Tetrahedron, 27, 1917 (1971).
P. J. Halls, R. A. Y. Jones, A. R. Katritzky, M. Snarey, and D. L. Trepanier, J. Chem. Soc., B. No. 10, 1320 (1971).
I. J. Ferguson, A. R. Katritzky, and D. M. Read, J. Chem. Soc., Perkin II, No. 6, 818 (1977).
Yu. Yu. Samitov, B. V. Unkovskii, I. P. Boiko, O. I. Zhuk, and Yu. F. Malina, Zh. Org. Khim., 9, 193 (1973).
Yu. Yu. Samitov, O. I. Zhuk, B. V. Unkovskii, and Yu. F. Malina, Zh. Org. Khim., 9, 201 (1973).
Yu. Yu. Samitov, O. I. Zhuk, O. P. Boiko, B. V. Unkovskii, and Yu. F. Malina, Zh. Org. Khim., 10, 1283 (1974).
I. P. Boiko, O. I. Zhuk, Yu. F. Malina, Yu. Yu. Samitov, and B. V. Unkovskii, Zh. Org. Khim., 11, 612 (1975).
I. J. Ferguson, A. R. Katritzky, and D. M. Read, Chem. Commun., No. 7, 225 (1975).
H. Booth and R. U. Lemeiux, Can. J. Chem., 49, 777 (1971).
A. A. Lapshova, Master's Dissertation, Ufa (1980).
O. I. Danilova, Yu. Yu. Samitov, I. P. Boiko, B. V. Unkovskii, Yu. F. Malina, F. N. Latypova, and T. O. Bordyukova, News in the Chemistry of Nitrogen-Containing Heterocycles [in Russian], Vol. 1, Riga (1979), p. 182.
J. M. Lehn, P. Linscheid, and F. G. Riddel, Bull. Soc. Chim. France, No. 3, 1172 (1968).
I. D. Blackburne, R. P. Tuke, R. A. Y. Jones, A. R. Katritzky, and K. A. F. Record, J. Chem. Soc., Perkin Trans. 2, No. 4, 332 (1973).
M. Hotokka, J. Mol. Struct., 51, 133 (1979).
T. A. Crabb, M. J. Hall, and R. O. Williams, Tetrahedron, 29, 3389 (1973).
F. A. Alimirzoev, A. A. Lapshova, V. V. Zorin, A. U. Stepanyants, V. P. Lezina, F. N. Latypova, S. S. Zlot-skii, and D. L. Rakhmankulov, Zh. Prikl. Khim., 53, 911 (1980).
E. D. Bergmann, D. Lavie, and S. Pinchas, J. Am. Chem. Soc., 73, 5662 (1951).
M. Senkus, U.S. Patent No. 2474792; Chem. Abstr., 44, 1131 (1950).
M. Senkus, U.S. Patent No. 2550646; Chem. Abstr., 45, 8038 (1951).
H. R. Nace and F. P. Goldberg, J. Am. Chem. Soc., 75, 3646 (1953).
M. J. Soulal and E. A. Twamley, British Patent No. 14444552; Chem. Abstr., 86, 29366 (1977).
H. Senkus, J. Am. Chem. Soc., 67, 1515 (1945).
K. Ito, H. Oba, and M. Sekiya, Chem. Pharm. Bull., 20, 2112 (1972).
S. Carlsson, Swedish Patent No. 132772; Chem. Abstr., 46, 6671 (1952).
W. Stuhmer and W. Heiwich, Chem. Ber., 84, 224 (1951).
G. Ficini and H. Normant, Bull. Soc. Chim. France, Nos. 11–12, 1454 (1957).
M. J. Soulal and E. A. Twamley, British Patent No. 1441749; Chem. Abstr., 86, 4929 (1977).
T. H. Fife and L. Hagopian, J. Am. Chem. Soc., 90, 1007 (1980).
W. J. Croxall and J. H. Mellema, U.S. Patent No. 2960508; Chem. Abstr., 55, 14482 (1961).
Hiles Laboratories, Inc., British Patent No. 889303; Chem. Abstr., 58, 1347 (1963).
A. N. Gafarov, A. N. Punegova, G. A. Marchenko, E. I. Loginova, and S. S. Novikov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 405 (1980).
R. Kotani, T. Kuroda, T. Isozaki, and S. Sumoto, Tetrahedron, 25, 4743 (1969).
A. B. Dashkevich and F. G. Shepel', Khim. Geterotsikl. Soedin., No. 5, 654 (1965).
M. J. Kalm, J. Org. Chem., 25, 1929 (1960).
B. F. Kukharev and A. S. Atavin, Khim. Geterotsikl. Soedin., No. 11, 1580 (1973).
H. Okano, A. Miyasu, H. Hamada, and R. Oda, Kobunshi Kagaku, 20, (221), 557 (1963); Chem. Abstr., 60, 14617 (1964).
H. Griengl and A. Bleikolm, Tetrahedron Lett., No. 5, 2565 (1975).
H. Griengl, A. Bleikolm, W. Grubbanor, and H. Soellrade, Ann., No. 3, 392 (1979).
H. Griengl and A. Bleikolm, Ann., No. 10, 1783 (1976).
V. V. Zorin, S. S. Zlot-skii, A. V. Il'yasov, and D. L. Rakhmankulov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 2097 (1976).
V. V. Zorin, S. S. Zlot-skii, A. V. Il'yasov, and D. L. Rakhmankulov, Zh. Org. Khim., 13, 2430 (1977).
V. V. Zorin, Master's Dissertation, Ufa (1977).
V. V. Zorin, V. F. Shuvalov, A. P. Moravskii, S. S. Zlot-skii, and. D. L. Rakhmankulov, Zh. Org. Khim., 15, 178 (1979).
A. A. Lapshova, V. V. Zorin, S. S. Zlot-skii, R. A. Karakhanov, and D. L. Rakhmankulov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 1197 (1980).
F. N. Latypova, V. V., Zorin, S. S. Zlot-skii, D. L. Rakhmankulov, and B. V. Unkovskii, Zh. Org. Khim., 12, 1369 (1976).
V. V. Zorin, F. N. Latypova, S. S. Zlot-skii, and D. L. Rakhmankulov, Zh. Prikl. Khim., 49, 2681 (1976).
V. V. Zorin, S. S. Zlot-skii, and D. L. Rakhmankulov, Zh. Prikl. Khim., 52, 447 (1979).
A. A. Lapshova, V. V. Zorin, S. S. Zlot-skii, R. A. Karakhanov, and. D. L. Rakhmankulov, Zh. Org. Khim., 16, 365 (1980).
A. A. Lapshova, V. V. Zorin, S. S. Zlot-skii, R. A. Karakhanov, and D. L. Rakhmankulov, Third Symposium on the Chemistry and Technology of Heterocyclic Compounds of Fossil Fuels (Summaries of Papers) [in Russian], Donetsk (1978), p. 71.
A. A. Lapshova, V. V. Zorin, S. S. Zlot-skii, R. A. Karakhanov, and. D. L. Rakhmankulov, All-Union Scientific-Technical Conference on the Replacement of Nutritive and Plant Raw Materials by Petrochemical Products in the Paint and Varnish Industry (Summaries of Papers) [in Russian], Ufa Petroleum Institute, Ufa (1978), p. 45.
D. L. Rakhmankulov and S. S. Zlot-skii, Khim. Geterotsikl. Soedin., No. 8, 1011 (1977).
A. A. Lapshova, V. V. Zorin, S. S. Zlot-skii, V. M. Zhulin, and D. L. Rakhmankulov, Zh. Org. Khim., 16, 1251 (1980).
A. A. Lapshova, V. V. Zorin, S. S. Zlot-skii, and D. L. Rakhmankulov, Zh. Org. Khim., 15, 2227 (1979).
A. A. Lapshova, V. V. Zorin, S. S. Zlot-skii, R. A. Karakhanova, and D. L. Rakhmankulov, News in the Chemistry of Nitrogen-Containing Heterocycles [in Russian], Vol. 2, 166 (1979).
V. V. Zorin, Scientific-Technical Conference on the Chemistry and Technology of Oxygen-Containing Heterocyclic Compounds [in Russian], Ufa (1979), p. 7.
A. A. Lapshova, V. V. Zorin, S. S. Zlot-skii, R. A. Karakhanov, and D. L. Rakhmankulov, First All-Union Conference on Organometallic Chemistry (Summaries of Papers), Part II, Moscow (1979), p. 279.
A. A. Lapshova, V. V. Zorin, S. S. Zlot-skii, R. A. Karakhanov, and D. L. Rakhmankulov, Zh. Org. Khim., 16, 1341 (1980).
F. N. Latypova, A. L. Aleksandrov, S. S. Zlot-skii, and D. L. Rakhmankulov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 4, 951 (1979).
S. A. Agisheva, A. L. Aleksandrov, V. S. Martem'yanov, S. S. Zlot-skii, and D. L. Rakhmankulov, Neftekhimiya, 15, 742 (1975).
G. A. Kovtun and A. L. Aleksandrov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 6, 1274 (1974).
E. M. Pliss, A. L. Aleksandrov, and M. M. Golikevich, Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2823 (1976).
G. Sh. Bakhturidze, A. L. Aleksandrov, and I. L. Edilashvili, Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 515 (1979).
Masuo Murakami, Kiyoshi Marase, and Toshiyasu Mase, Japanese Patent No. 21421; Ref. Zh. Khim., 8N290P (1973).
Sumitomo Chemical Co. Ltd., Japanese Patent No. 20626; Chem. Abstr., 66, 55491 (1967).
D. Banerjee, S. Mukerji, N. L. Dutt, and B. N. Mitra, Indian J. Chem., 9, 799 (1971).
E. C. Teache, U.S. Patent No. 2350547; Chem. Abstr., 81, 13490 (1974).
E. G. Teache, U.S. Patent No. 2605586; Chem. Abstr., 85, 192713 (1976).
E. G. Teache, U.S. Patent No. 566019; Ref. Zh. Khim., 20385P (1977).
K. P. Dorschner and J. A. Albiright, U.S. Patent No. 534824; Ref. Zh. Khim., 170435P (1978).
H. Sidi and H. R. Johnson, French Patent No. 2279737; Chem. Abstr., 85, 162041 (1976).
H. Sidi and H. R. Johnson, U.S. Patent No. 3890264; Chem. Abstr., 83, 165910 (1975).
H. Sidi and H. R. Johnson, U.S. Patent No. 3962271; Chem. Abstr., 85, 177395 (1976).
J. H. Hunsucker, U.S. Patent No. 2512980; Chem. Abstr., 84, 74255 (1976).
Imperial Chemical Industries, British Patent No. 1015794; Chem. Abstr., 64, 17609 (1965).
H. Tesmann, P. Busch, and H. U. Stracke, U.S. Patent No. 2657715; Chem. Abstr., 89, 220749 (1978).
L. V. Semenov, A. A. Gaile, Li Gvan Khun, E. A. Ershova, and V. A. Proskuryakov, Zh. Prikl. Khim., 51, 234 (1978).
A. A. Gaile, N. F. Grishchenko, A. P. Zakharov, V. L. Klimenko, P. I. Lastovkin, V. A. Proskuryakov, and L. V. Semenov, USSR Inventor's Certificate No. 611899; Byull. Izobret., No. 23, 73 (1978).
A. Lai and J. Ta-Yuan, U.S. Patent No. 4104254; Chem. Abstr., 90, 104942 (1979).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 435–449, April, 1982.
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Rakhmankulov, D.L., Zorin, V.V., Latypova, F.N. et al. Synthesis, structure, and properties of 1,3-oxazacycloalkanes (review). Chem Heterocycl Compd 18, 321–333 (1982). https://doi.org/10.1007/BF00503543
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DOI: https://doi.org/10.1007/BF00503543