The chemistry of amidrazones

The Chemistry of Amidines and Imidates

Volumn , Issue , 2010, Pages 491-545

  Watson, K M ^a   Neilson, D G ^a  

^a UNIVERSITY OF DUNDEE   (United Kingdom)

Author keywords

Acid halides; Esters; Heterocycles; Hydrazides; Nitriles

Indexed keywords

ACID HALIDES; HETEROCYCLES; HYDRAZIDES; NITRILES;

ESTERS;

EID: 84958668579     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470771495.ch10     Document Type: Chapter

References (183)

1. D. G. Neilson, R. Roger, W. M. Heatlie and L. R. Newlands, Chem. Revs., 70, 151 (1970).
2. H. Rapoport and R. M. Bonner, J. Am. Chem. Soc., 72, 2783 (1950).
3. Nomenclature Section, Chem. Abstracts, 56, 51N (1962).
4. F. H. Case, J. Org. Chem., 30,931 (1965).
5. S. Kubota, Y. Koida, T. Kosaka and O. Kirino, J. Pharm. Bull. (Japan., 18, 1696 (1970).
6. F. H. Case, J. Heterocyclic Chem., 5, 223 (1968).
7. Y. Kato and I. Hirao, Bull. Kyushu Inst. Tech., 15, 57 (1965), referred to in reference 106.
8. H. C. Brown and D. Pilipovich, J. Am. Chem. Soc., 82, 4700 (1960).
9. D. Genthe, Deut. Luft-Raumfahrt, Forschungber., 1970 DLR FB 70 (52);
10. D. Genthe, Chem. Abstr., 75, 65760r (1971).
11. P. M. Hergenrother, J. Polym. Sci., Part A., 7, 945 (1969).
12. D.D. Libman and R. Slack, J. Chem. Soc., 2253 (1956).
13. J. F. Geldard and F. Lions, J. Org. Chem., 30, 318 (1965).
14. S. Kubota, O. Kirino, Y. Koida and K. Miyake, J. Pharm. Soc. Japa., 92, 275 (1972).
15. V. P. Wystrach, Heterocyclic Compounds, Vol. 8 (Ed. R. C. Elderfield), John Wiley and Sons, New York, 1967, p. 113.
16. T. K. Brotherton and J. W. Lynn, Chem. Revs., 59, 841 (1959).
17. K. Matsuda and L. T. Morin, J. Org. Chem., 26, 3783 (1961).
18. L. T. Morin and K. Matsuda, U.S. Patent 3,033,893 (1962);
19. L. T. Morin and K. Matsuda, Chem. Abstr., 51, 14948d (1962).
20. R. G. Haldeman, L. T. Morin and K. Matsuda, U.S. Patent 3,075,013 (1963);
21. R. G. Haldeman, L. T. Morin and K. Matsuda, Chem. Abstr., 58, 11276a (1963).
22. G. W. McNeely, Diss. Abstr., Int. B., 31, 2570 (1971).
23. M. M. Fein, J. Bobinski, J. E. Paustian, D. Grafstein and M. S. Cohen, Inorg. Chem., 4, 422 (1965).
24. J. Bobinski, M. M. Fein and D. Grafstein, U.S. Patent 3,288,802 (1966);
25. J. Bobinski, M. M. Fein and D. Grafstein, Chem. Abstr., 66, 39498f (1967).
26. W. Walter and H. Weiss, Ann. Chem., 758, 162 (1972).
27. R. Fuks, Tetrahedro., 29, 2147 (1973).
28. T. Kauffmann, J. Hansen, C. Kosel and W. Schoeneck, Ann. Chem., 656, 103(1962).
29. T. Kauffmann, S. Spaude and D. Wolf, Chem. Ber., 97, 3436 (1964).
30. T. Kauffmann and L. Ban, Chem. Ber., 99, 2600 (1966).
31. G. C. Wright, R. P. Halliday and C. S. Davis, J. Pharm. Sci., 59, 105 (1970).
32. K. H. Linke, R. Taubert, K. Bister, W. Bornatsch and B. J. Liem, Z. Naturforsch. B., 26, 296 (1971).
33. V. S. Garkusha-Bozhko, S. M. Baranov and O. P. Shvaika, Ukr. Khim. Zh., 38, 171 (1972);
34. V. S. Garkusha-Bozhko, S. M. Baranov and O. P. Shvaika, Chem. Abstr., 77, 34426y (1972).
35. C. L. Stevens, R. C. Freeman and K. Noll, J. Org. Chem., 30, 3718 (1965).
36. F. Kurzer and D. R. Hanks,J. Chem. Soc. (C), 1375 (1968).
37. F. Kurzer and K. Douraghi-Zadeh, Chem. Revs., 67, 107 (1967).
38. C. Grundmann, Angew. Chem. (Int. Ed.), 2, 309 (1963).
39. R. Roger and D. G. Neilson, Chem. Revs., 61, 179 (1961).
40. H. Neunhoeffer and H.-W. Fruhauf, Ann. Chem., 760, 102 (1972).
41. E. C. Taylor and S. F. Martin, J. Org. Chem., 37, 3958 (1972).
42. V. Uchytilova, P. Fiedler, M. Prystas and J. Gut, Coll. Czech. Chem. Commun., 36, 1955 (1971).
43. M. Brugger, H. Wamhoff and K. Korte, Ann. Chem., 755, 101 (1972).
44. M. R. Atkinson and J. B. Polya, J. Chem. Soc., 3319 (1954).
45. E. E. Glover, K. T. Rowbottom and D. C. Bishop, J. Chem. Soc., Perkin I, 2927 (1972).
46. H. G. O. Becker, G. Goermar and H.-J. Timpe, J. Prakt. Chem., 312, 601 (1970).
47. R. Kraft, H. Paul and G. Hilgetag, Chem. Ber., 101, 2028 (1968).
48. Y. Charbonnel and J. Barrans, C.R. Acad. Sci. Paris, ., 272, 1675 (1970).
49. G. S. Gol'din, V. G. Poddubnyi, A. A. Simonova, G. S. Shor and E. A. Rybakov, Zh. Org. Khim., 5, 1404 (1969).
50. G. S. Gol'din, V. G. Poddubnyi, A. A. Simonova, A. B. Kamenskii and G. S. Shor, J. Gen. Chem., 40, 1281 (1970).
51. G. S. Gol'din, M. V. Maksakova and A. N. Kol'tsova, J. Gen. Chem., 43, 317(1973).
52. F. A. Hussein and A. A. Kadir, J. Indian Chem. Soc., 45, 729 (1968).
53. T. Mukaiyama and S. Ono, Tetrahedron Letters, 3569 (1968).
54. E. P. Nesynov, M. M. Besprozvannaya and P. S. Pel'kis, Zh. Org. Khim., 6, 805(1970).
55. E. Bisagni, J. P. Marquet and J. Andre-Louisfert, Bull. Soc. Chim. France, 1483(1972).
56. H. Reimlinger, J. M. Vandewalle and W. R. F. Lingier, Chem. Ber., 103, 1960 (1970).
57. R. F. Smith, D. S. Johnson, C. L. Hyde, T. C. Rosenthal and A. C. Bates, J. Org. Chem., 36, 1155 (1971).
58. R. F. Smith, D. S. Johnson, R. A. Abgott and M. J. Madden, J. Org. Chem., 38, 1344 (1973).
59. Z. Csuros, R. Soos, I. Bitter and J. Palinkas, Acta Chim. Acad. Sci. Hung., 69, 361 (1971);
60. Z. Csuros, R. Soos, I. Bitter and J. Palinkas, Chem. Abstr., 75, 129,751y (1971).
61. W. Hoyle, J. Chem. Soc. (C), 690 (1967).
62. H. Meerwein, W. Florian, N. Schön and G. Stopp, Ann. Chem., 641, 1 (1961).
63. W. J. van der Burg, Rec. Trav. Chem., 74, 257 (1955).
64. A. Spassov and E. Golovinsky, J Gen. Chem., 32, 3330 (1962).
65. A. Spassov, E. Golovinsky and G. Demirov, Chem. Ber., 99, 3734 (1966).
66. H. Neunhoeffer and H. Hennig, Chem. Ber., 101, 3947 (1968).
67. W. Walter, H. Weiss and K.-J. Reubke, Ann. Chem., 736, 166 (1970).
68. I. Hagedorn and H.-D. Winkelmann, Chem. Ber., 99, 850 (1966).
69. V. R. Grashey, M. Baumann and H. Bauer, Chem. Ztg., 96, 224 (1972).
70. R. Fusco and P. Dalla Croce, Gazz. Chim. Ital., 99, 69 (1969).
71. J. Perronet and P. Girault, German Patent 2,146,192, (1972);
72. J. Perronet and P. Girault, Chem. Abstr., 77, 34128c (1972).
73. G. Ponzio, Gazz. Chim. Ital., 40, 77 (1910).
74. H. C. Brown and M. T. Cheng,J. Org. Chem., 27, 3240(1962).
75. G. V. Boyd and A. J. H. Summers, J. Chem. Soc. (C), 409 (1971).
76. O. P. Shvaika and V. I. Fomenko, Dokl. Acad. Nauk SSSR (Chem.), 200, 134 (1971);
77. O. P. Shvaika and V. I. Fomenko, Chem. Abstr.,16, 59542a (1972).
78. H. G. O. Becker, D. Beyer, G. Israel, R. Müller, W Riediger and H.-J. Timpe, J. Prakt. Chem., 312, 669 (1970).
79. H. Kohn and R. A. Olofson,J. Org. Chem., 37, 3504 (1972).
80. D. Jerchel and H. Fischer, Ann. Chem., 574, 85 (1951).
81. F. Moczarand L. Mester, Bull. Soc. Chim. France, 186 (1962).
82. M. Regitz and B. Eistert, Chem. Ber., 96, 3120 (1963).
83. D. Jerchel and R. Kuhn, Ann. Chem., 568, 185 (1950).
84. D. Jerchel and W. Wotichy, Ann. Chem., 605, 191 (1957).
85. H. Hellmann and W. Schwiersch, Chem. Ber., 94, 1868 (1961).
86. B.-G. Baccar and J. Barrans, C.R. Acad. Sci. Paris, ., 263, 743 (1966).
87. B.-G. Baccar, R. Mathis, A. Seeches, J. Barrans and F. Mathis, J. Mol. Struct., 7, 369 (1971).
88. R. R. Tarasyants, G. M. Petrova, G. S. Gol'din, V. G. Poddubnyi, S. G. Fedorov, and A. A. Simonova, J. Gen. Chem., 43, 495 (1973).
89. H.-J. Hofmann and M. Scholz, J. Prakt. Chem., 313, 349 (1971).
90. G. S. Gol'din, M. V. Maksakova and A. N. Kol'tsova, J. Gen. Chem., 42, 1351 (1972).
91. F. H. Case, J. Heterocyclic Chem., 10, 353 (1973).
92. A. S. Shawali, A. Osman and H. H. Hassaneen, Indian J. Chem., 10, 965(1972).
93. H. C. Brown and R. Pater, J. Org. Chem., 30, 3739 (1965).
94. G. S. Gol'din, V. G. Poddubnyi, A. A. Simonova, E. V. Orlova and G. S. Shor, Zh. Org. Khim., 5, 1411 (1969).
95. H. Neunhoeffer, F. Weischedel and V. Böhnisch, Ann. Chem., 750, 12 (1971).
96. G. S. Gold'din, V. G. Poddubnyi, E. V. Orlova and A. V. Kisin, Zh. Org. Khim., 9, 517 (1973).
97. J. H. Boyer, Heterocyclic Compounds, Vol. 7 (Ed. R. C. Elderfield), John Wiley and Sons, New York, 1961, pp. 384-461.
98. J. P. Horwitz, Heterocyclic Compounds, Vol. 7 (Ed. R. C. Elderfield), John Wiley and Sons, New York, 1961, pp. 720-796.
99. R. L. Jones and J. R. Kershaw, Rev. Pure Appl. Chem., 21, 23 (1971).
100. H. Rcimlinger, W. R. F. Lingier and J. J. M. Vandewalie, Chem. Ber., 104, 639(1971).
101. J. E. Francis, U.S. Patent 3,354,164 (1967);
102. J. E. Francis, Chem. Abstr., 69, 36142m (1968).
103. H. Moeller, German Patent 2,113,731 (1972);
104. H. Moeller, Chem. Abstr., 77, 164709d (1972).
105. M. Saga and T. Shono, J. Polymer. Sci., B4, 869 (1966).
106. M. L. Hoefle and A. Holmes, French Patent 2,100,863 (1972);
107. M. L. Hoefle and A. Holmes, Chem. Abstr.,77,164710x (1972).
108. M. Yanai, T. Kinoshita, S. Takeda, M. Nishimura and T. Kuraishi, Chem. Pharm. Bull., Japa., 20, 1617 (1972).
109. K. T. Potts and C. R. Surapaneni, J. Heterocyclic Chem., 7, 1019 (1970).
110. A. Spassov, E. Golovinsky and G. Russev, Chem. Ber., 96, 2996 (1963).
111. I. Hirao, Y. Kato and H. Tateishi, Bull. Chem. Soc. Japa., 45, 208 (1972).
112. K. T. Potts and S. W. Schneller, J. Heterocyclic Chem., 5, 485 (1968).
113. F. H. Case, J. Heterocyclic Chem., 7, 1001 (1970).
114. P. M. Hergenrother, J. Heterocyclic Chem., 6, 965 (1969).
115. A. Spassov and G. Demirov, Chem. Ber., 101,4238(1968).
116. A. Spassov and G. Demirov, Chem. Ber., 102, 2530 (1969).
117. P. M. Hergenrother, Macromolecule., 3, 10(1970).
118. I. Hirao, Y. Kato, T. Hayakawa and H. Tateishi, Bull. Chem. Soc. Japa., 44, 780 (1971).
119. P. Westermann, H. Paul and G. Hilgetag. Chem. Ber., 97, 528 (1964).
120. B. Stanovnik and M. Tisler, Tetrahedron Letters, 2403 (1966).
121. V. V. Mezheritskii, E. P. Olekhnovich and G. N. Dorofeenko, Russian Chem. Revs., 42, 392 (1973).
122. R. H. DeWolfe, Carboxylic Ortho Acid Derivatives, Academic Press, New York, 1970.
123. W. Ried and P. Schomann, Ann. Chem., 714, 122 (1968).
124. H. Weidingerand J. Krantz, Chem. Ber., 96, 1064 (1963).
125. A. Spassov and G. Demirov, Chem. Ber., 103, 3867 (1970).
126. F. H. Case, J. Heterocyclic Chem., 8, 173 (1971).
127. P. M. Hergenrother and L. A. Carlson, J. Polymer Sci., A-18, 1003 (1970).
128. S. Naqui and V. R. Srinivasan, Indian J. Chem., 3, 162 (1965).
129. D.-I. Shiho and S. Tagami, J. Am. Chem. Soc., 82, 4044 (1960).
130. G. Pifferi and P. Consonni, J. Heterocyclic Chem., 9, 581 (1972).
131. A. Pollack, B. Stanovnik and M. Tisler, Tetrahedro., 24, 2623 (1968).
132. H. Neunhoeffer and H. Hennig, Chem. Ber., 101, 3952 (1968).
133. H. Neunhoeffer, H. Hennig, N.-W. Frühauf and M. Mutterer, Tetrahedron Letters, 3147 (1969).
134. H. Paul, S. Chatterjee and G. Hilgetag, Chem. Ber., 101, 3696 (1968).
135. H. Neunhoeffer, L. Motitschke, H. Hennig and K. Ostheimer, Ann. Chem., 760, 88 (1972).
136. P. M. Hergenrother and D. E. Kiyohara, J. Macromol. Sci. Chem., 5, 365 (1971).
137. V. Uchytilova, P. Fiedler and J. Gut, Coll. Czech. Chem. Comm., 37, 2221 (1972).
138. W. Ried and P. Schomann, Ann. Chem., 714, 128 (1968)
139. F. H. Case,J. Heterocyclic Chem., 9, 457 (1972).
140. M. Brugger, H. Wamhoff and F. Korte, Ann. Chem., 758, 173 (1972).
141. A. Spassov, E. Golovinsky and G. Russev, Chem. Ber., 99, 3728 (1966).
142. H. Neunhoeffer and F. Weischedel, Ann. Chem., 761, 34 (1972).
143. W. Ried and P. Schomann, Ann. Chem., 701, 92 (1967).
144. W. Ried and P. Schomann, Ann. Chem., 714, 140 (1968).
145. M. Brugger, H. Wamhoff and F. Körte, Ann. Chem., 757, 100 (1972).
146. A. Spassov, E. Golovinsky and G. Demirov, Chem. Ber., 98, 932 (1965).
147. H. Reimlinger, W. R. F. Lingier, J. J. M. Vandewalle and E. Goes, Synthesis, 433, (1970).
148. R. Huisgen, R. Grashey, M. Seidel, H. Knupfer and R. Schmidt, Ann. Chem., 658, 169 (1962).
149. H. Reimlinger, F. Billiau and W. R. F. Lingier, Synthesis, 260 (1970).
150. W. Walterand H. Weiss, Ann. Chem., 1294 (1973).
151. T. Bany, Rocz. Chem., 42, 247 (1968);
152. T. Bany, Chem. Abstr., 69, 67340d (1968).
153. T. Bany and H. Dobosz, Rocz. Chem., 46, 1123 (1972);
154. T. Bany and H. Dobosz, Chem. Abstr., 77, 164587n (1972).
155. D. Frank, W. Brodowski and P. Hentschel, German Patent 2,061,895 (1972);
156. D. Frank, W. Brodowski and P. Hentschel, Chem. Abstr., 77, 102430x (1972).
157. G. S. Gol'din, V. G. Poddubnyi, E. S. Smirnova and V. P. Kozyukov, J. Gen. Chem., 43, 342 (1973).
158. H. Reimlinger, Chem. and Ind., 1082 (1970).
159. T. Kuraishi and R. N. Castle, J. Heterocyclic Chem., 1, 42 (1964).
160. Y. Charbonnel and J. Barrans, C.R. Acad. Sci. Paris, C., 274, 2209 (1972).
161. M. J. S. Dewar, R. Golden and P. A. Spanninger, J. Am. Chem. Soc., 93, 3298 (1971).
162. M. Busch and R. Ruppenthal, Ber. dt. chem. Ges., 43, 3001 (1910).
163. S. Hünig, W. Brenninger, H. Geiger, G. Kaupp, W. Kniese, W. Lampe, H. Quast, R. D. Rauschenbach and A. Schütz, Angew. Chem. (Int. Ed., 7, 335 (1968).
164. N. I. Abramova, R. O. Matevosyan, Yu. A. Abramov, V. N. Yakovleva, A. K. Chirkov, L. A. Perelyaeva, V. A. Gubanov and V. I. Koryakov, Khim. Gcterotsikl., Soedi., 7, 1484 (1971);
165. N. I. Abramova, R. O. Matevosyan, Yu. A. Abramov, V. N. Yakovleva, A. K. Chirkov, L. A. Perelyaeva, V. A. Gubanov and V. I. Koryakov, Chem. Abstr., 77, 34409v (1972).
166. M. Genchev, R. Pelova and G. Demirev, Natura (Plovdiv) 2, 41 (1968);
167. M. Genchev, R. Pelova and G. Demirev, Chem. Abstr., 72, 96145m (1970).
168. A. A. Schilt, W. E. Dunbar, B. W. Gandrud and S. E. Warren, Talant., 17, 649(1970).
169. J. F. Geldard and,F. Lions, Inorg. Chem., 2, 270 (1963).
170. G. Rouschias and B. L. Shaw, J. Chem. Soc. (A), 2097 (1971).
171. T. Kauffmann, L. Ban and D. Kuhlmann, Angew. Chem. (Int. Ed.., 6, 256(1967).
172. C. D. Wright, U.S. Patent 3,202,659 (1965);
173. C. D. Wright, Chem. Abstr., 63, 18123f (1965).
174. J. Kunde and R. Gehm, German Patent 1,186,618 (1965);
175. J. Kunde and R. Gehm, Chem. Abstr., 62, 10649e (1965).
176. A. Schoepf and G. Meyer, U.S. Patent 3,560,453 (1971);
177. A. Schoepf and G. Meyer, Chem. Abstr., 74, 88572z (1971).
178. C. S. Davis, U.S. Patent 3,458,500 (1969);
179. C. S. Davis, Chem. Abstr., 71, 81223r (1969).
180. T. L. Fridinger and J. E. Robertson, J. Med. Chem., 12, 1114 (1969).
181. T. Pantev, N. Bokova, I. Baev and I. Nikolov, Rentgenol. Radiol., 10, 11 (1971);
182. T. Pantev, N. Bokova, I. Baev and I. Nikolov, Chem. Abstr., 75, 95153n (1971).
183. B. Prescott and G. Caldes, J. Pharm. Sci., 59, 101 (1970).