The chemistry of thiohydrazonates and their utility in organic synthesis

Journal of Sulfur Chemistry

Volumn 26, Issue 3, 2005, Pages 267-303

  Shawali, Ahmad Sami ^a   Mosselhi, Mosselhi A N ^a  

^a CAIRO UNIVERSITY   (Egypt)

Author keywords

Biological activity; Cyclization; Heterocycles; Hydrazonoyl halides; Oxidation; Rearrangement; Substitution

Indexed keywords

BIOACTIVITY; SYNTHESIS (CHEMICAL);

CYCLIZATIONS; HETEROCYCLES; HETEROCYCLIC RINGS; HYDRAZONOYL HALIDE; ORGANIC SYNTHESIS; REARRANGEMENT; RING SYSTEMS; SPECTROSCOPIC PROPERTY; TITLE COMPOUNDS;

CYCLIZATION;

EID: 30344466969     PISSN: 17415993     EISSN: 17416000     Source Type: Journal    
DOI: 10.1080/17415990500124586     Document Type: Review

References (169)

1. A.S. Shawali, C. Parkanyi. J. Heterocycl. Chem., 17, 833 (1980).
2. A.S. Shawali. Heterocycles, 20, 2239 (1983).
3. A.S. Shawali. Chem. Rev., 93, 2731 (1993).
4. A.S. Shawali, M.A. Abdallah. Adv. Heterocycl. Chem., 63, 277 (1995).
5. A.S. Shawali, S.M. Elsheikh. J. Heterocycl Chem., 38, 541 (2001).
6. A.S. Shawali, M.A. Mosselhi. J. Heterocycl. Chem., 40, 725 (2003).
7. D.O. Neilson, R. Rogers, W.M. Heatlie, L.R. Newlands. Chem. Rev., 70, 151 (1969).
8. A.S. Shawali, S.M. Elsheikh, C. Parkanyi. J. Heterocycl. Chem., 40, 207 (2003).
9. A.O. Abdelhamid, M.N. Alkathiri. Phosphorus, Sulfur, Silicon, 119, 181 (1996).
10. P. Frohberg, C. Kupfer, P. Stenger, U. Baumeister, P. Nuhn. Arch. Pharm. (W), 328, 505 (1995).
11. A.O. Abdelhamid, F.F. Abdelmegeid, N.M. Hassan, H.F. Zohdi. J. Chem. Res. (S) 492, (M) 3036 (1995).
12. A.O.A. Eltoum, N.J. O'Reilly, A.E. Tipping. J. Fluorine Chem., 65, 101 (1993).
13. H.M. Hassaneen, A.S. Shawali, N.M. Elwan, N. Abounada. Sulfur Lett., 13, 273 (1992).
14. T. Benincori, R. Fusco, F. Sannicolo'. Gazz. Chim. Ital., 120, 635 (1990).
15. (a) M.K.A. Ibrahim, M.S. Elgharib, A.M. Farag, A.H. Elghandour. Indian J. Chem., 27B, 836 (1988);
16. (b) A.O. Abdelhamid, M.N. Al-Kathiri. Phosphorus, Sulfur & Silicon, 49, 181 (1996).
17. H.M. Hassaneen, H.A.H. Mousa, N.M. Abed, A.S. Shawali. Heterocycles, 27, 695 (1988).
18. H.M. Hassaneen, A.O. Abdelhamid, A.A. Fahmi, A.S. Shawali. J. Heterocycl. Chem., 22, 395 (1985).
19. J.E. Rowe, A.F. Hegarty. J. Org. Chem., 49, 3083 (1984).
20. N. Almirante, L. Forti. J. Heterocycl. Chem., 20, 1523 (1983).
21. A.S. Shawali, H.M. Hassaneen, N.F. Eweiss. J. Appl. Chem. Biotechnol., 28, 864 (1978).
22. A.S. Shawali, H.M. Hassaneen. Bull. Chem. Soc. Jpn., 50, 2827 (1977).
23. A.S. Shawali, H.M. Hassaneen. Indian J. Chem., 14B, 425 (1976).
24. A.J. Elliott, P.D. Callaghan, M.S. Gibson, S.T. Nemeth. Can. J. Chem., 53, 1484 (1975).
25. H. Emam, A.O. Abdelhamid. Phosphorus, Sulfur, Silicon & Rel. Elements, 131, 37 (1997).
26. H.H. Alnima, A.A. Ibrahim, W. Farig. Indian J. Chem., 34(B), 736 (1995).
27. H.M. Hassaneen, A.S. Shawali, N.M. Elwan, A. Ibrahim. Arch. Pharm., 14, 266 (1991).
28. N.A. Ismail. Egypt. J. Pharm. Sci., 32, 961 (1991).
29. A.O. Abdelhmid, F.H.H. Elshiaty. Phosphorus & Sulfur, 39, 45 (1988).
30. A.M. Farag, M.S. Algharib. Org. Prep. Proc. Int., 20, 521 (1988).
31. E.M. Kandeel, H.H.S. Alnima, M.H. Elnagdi. Polish J. Chem., 57, 327 (1983);
32. Chem. Abstr., 101, 7093v (1984).
33. A.M. Abdelfattah, H.A. Daboun, S.M. Hussein. Egypt. J. Chem., 26, 409 (1983);
34. Chem. Abstr., 101, 230419h (1984).
35. A.A. Mahfouz, F.M. Elhabashy. Arch. Pharmacol Res., 13, 9 (1990).
36. A.O. Abdelhamid, F.A. Attaby. J. Heterocycl. Chem., 28, 41 (1991).
37. R.N. Butler, E.P. NiBhradalgh, K.J. Fitzgerald. J. Chem. Res. (S), 306 (1993).
38. I.M. Abbas, M.A. Abdallah, M. Mosselhi, M.A.N., S.Z. Mohamed, A.S. Shawali. J. Chem. Res. (S), 308 (1994).
39. M.A. Abdallah, M.A.N. Mosselhi, I.M. Abbas, A.A. Fahmi, A.S. Shawali. J. Chem. Res. (S), 370 (1995).
40. R.N. Butler, E.O. Ni Bhradalgh, P. McArdle, D. Cunningham. J. Chem. Res., (S), 224, (M) 1401 (1995).
41. A.K. Mansour, N.M. Elwan, H.A. Abdelhadi, H.M. Hassaneen. Sulfur Lett., 18, 105 (1995).
42. M.A. Abdallah, M.A.N. Mosselhi, S.M. Riyadh, A.E. Harhash, A.S. Shawali. J. Chem. Res., (S) 700, (M) 3038 (1998).
43. A.S. Shawali, A.A. Elghandour, S.M. Elsheikh. Heteroatom Chem., 11, 87 (2000).
44. A.S. Shawali, S.M. Gomha. J. Prakt. Chem., 342, 599 (2000).
45. H.A. Elfahham, K.U. Sadek, G.E.H. Elgemie, M.H. Elnagdi. Chem. Lett., 119 (1982).
46. H.A. Elfahham, K.U. Sadek, G.E.H. Elgemie, M.H. Elnagdi. J. Chem. Soc. Perkin Trans I, 2663 (1982).
47. J. Perronnet, P. Girault. Bull. Soc. Chim. Fr., 2843 (1973).
48. Ya.V. Zachinyaev, M.L. Petrov, A.N. Frolkov, V.N. Chistokletov, A.A. Petrov. Zh. Org. Khim., 16, 938 (1980);
49. Chem. Abstr., 93, 204598f (1980).
50. A.H. Elghandour, M.K.A. Ibrahim, B. El-Badry, H.K. Waly. Phosphorus, Sulfur, Silicon, 88, 147 (1994).
51. N.A. Terent'eva, M.L. Petrov, K.A. Potekhin, Yu.T. Struchkov, V.A. Galishev. Zh. Org. Khim., 30, 344 (1994);
52. Chem. Abstr. 123, 143737q (1995).
53. N.A. Terent'eva, M.L. Petrov, O.V. Shishkin, Yu.T. Struchkov, K.A. Potekhin, V.A. Galishev. Zh. Org. Khim., 31, 891 (1995);
54. Chem. Abstr., 124, 2889202z (1996).
55. A.R. Katritzky, I. Ghiviriga, D.C. Oniciu, F. Soti. J. Heterocycl. Chem., 33, 1927 (1996).
56. N. Troiani, P. Ponola, F. Gozzo, S. Lorusso. Ger. Offen. 2,436,544 (1975); Chem. Abstr., 83, 78829k (1975).
57. S. Trotto, J.A. Furch, D.G. Kuhn, D.A. Hunt. Eur. Pat. Appl. EP, 709,372 (1996); Chem. Abstr., 125, 58090v (1996).
58. F. Abu-Awwad, B. Abu-Taher. Asian J. Chem., 15, 25 (2003).
59. B. Joseph, P. Rolin. J. Carbohydr. Chem., 12, 1127 (1993).
60. B. Joseph, P. Rollin. J. Chem. Res. (S), 128, (M) 770 (1994).
61. A.S. Shawali, M.A.N. Mosselhi, M.A. Abdallah, T.M. Farghaly. Monatsh. Chem., 135, 211 (2004).
62. Ya.V. Zachinyaev, A.I. Bobrov. Ukr. Khim. Zh., 53, 1200 (1987);
63. Chem. Abstr., 109, 230413k (1988).
64. T. Benincori, E. Brenna, F. Sannicolo', L. Trimarco, T. Pilati. Gazz. Chim. Ital., 123, 531 (1993).
65. M.Z.A. Badr, A.M. Mahmoud, S.A. Mahgoub, Z.A. Hozien. Bull. Chem. Soc. Jpn., 61, 1339 (1988).
66. M.A.N. Mosselhi, M.A. Abdallah, I.M. Abbas, S.M. Mohammed, A.S. Shawali. J. Chem. Res. (S), 83, (M) 646 (1995).
67. A.N. Krasovsky, A.P. Andrushko, A.M. Demchenko. Khim. Geterot. Soed., 37, 496 (2001);
68. Chem. Abstr., 136, 216700c (2002).
69. A.J. Elliott, M.S. Gibson. J. Org. Chem., 45, 3677 (1980).
70. T.E. Glotova, A.S. Nakhmanovich, M.V. Sigalov. Khim. Geterotsikl. Soedin, 680 (1989);
71. Chem. Abstr. 112, 98465j (1990).
72. F. Kurzer, J.L. Secker. Tetrahedron, 37, 1429 (1981).
73. R. Huisgen, J. Sauer, M. Seidel. Chem. Ber., 94, 2503 (1961).
74. H. Kristinsson, T. Winkler, M. Molinkopf. Helv. Chim. Acta, 69, 333 (1986).
75. J.P.F. Dunstan, G.M. Elsey, R.A. Russell, G.P. Savage, G.W. Simpson, E.R.T. Tiekink. Aust. J. Chem., 51, 499 (1998).
76. M. Muhlstadt, L. Weber, P. Birner. J. Chem. Soc. Perkin Trans II, 821 (1988).
77. F. Kurzer, K.M. Doyle. J. Chem. Soc. Perkin Trans I, 1873 (1986).
78. B. Chuong, T. Lehmann. Z. Chem., 30, 133 (1990);
79. Chem. Abstr., 113, 78351m (1990).
80. A.S. Shawali, H.M. Hassaneen, S.M. Sherif. J. Heterocycl. Chem., 17, 1745 (1980).
81. K. Martens, A. Scheunemann, K. Drexler, H. Dehne, H. Reinke, M. Michalik. Molecules, 6, 540 (2001).
82. R.N. Hanley, W.D. Ollis, C.A. Ramsden, I.S. Smith. J. Chem. Soc. Perkin Trans. 1, 744 (1979).
83. G. Mloston, A. Linden, H. Heimgartne. Helv. Chim, Acta, 79, 31 (1996).
84. A.S. Shawali, I.F. Zeid, M.H. Abdelkader, A.A. Elsherbini, F.M.A. Altalbawy. J. Chin. Chem. Soc., 48, 65 (2001).
85. M.A.N. Mosselhi, M.A. Abdallah, Y.F. Mohamed, A.S. Shawali. Phosphorus, Sulfur, Silicon, 177, 487 (2002).
86. T. Benincori, F. Sannicolo. J. Org. Chem., 53, 1309 (1988).
87. A.J. Elliott, M.S. Gibson, M.M. Kayser, Q.A. Pawelchak. Can. J. Chem., 51, 4115 (1973).
88. A.T. Hutton, H.M.N.H. Irving. J. Chem. Soc. Chem. Commun., 763 (1980).
89. H. Takahashi, O. Yamada, I. Hiroaki, K.N. Takadhi. J. Raman Spectrosc., 19, 305 (1988);
90. Chem. Abstr., 109, 159158y (1988).
91. H. Takahashi. Spectrochim, Acta, Part A, 44A, 1409 (1988).
92. A.T. Hutton, H.M.N.H. Irving. J. Chem. Soc. Perkin Trans 2, 1117 (1982).
93. U.W. Grummt, H. Langbein, R. Noeske, G. Roebisch. J. Photochem., 24, 53 (1984).
94. J. Guillerez, C. Pascard, T. Prange. J. Chem. Res. (S), 308 (1978).
95. A.T. Hutton, H.M.N.H. Irving, L.R. Nassimbeni. Acta Crystallogr, B36, 2071 (1980).
96. A.F. Hegarty, J.A. Kearny, F.L. Scott. J. Chem. Soc. Perkin Trans II, 1422 (1973).
97. M.A.N. Mosselhi, M.A. Abdallah, S.M. Riyadh, A.E. Harhash, A.S. Shawali. J. Prakt. Chem., 340, 160 (1998).
98. A.K. Mansour, N.M. Elwan, H.A. Abdelhadi, H.M. Hassaneen. Sulfur Lett., 18, 105 (1995).
99. A.S. Shawali, M.A. Abdallah, I.M. Abbas, G.M. Eid. J. Chin. Chem. Soc., 51, 351 (2004).
100. (a) A.O. Abdelhamid, F.A. Attaby, F. Khalifa, S.S. Ghabrial. Arch. Pharmacal. Res., 15, 14 (1992),
101. (b) A.O. Abdelhamid, F.F. Abdelmageid, N.M. Hassan, H.F. Zohdi. J. Chem. Res. (S), 492, (M) 3036 (1995).
102. J.E. Rowe, D.A. Papanelopoulos. Aust. J. Chem., 48, 2041 (1995).
103. M.D. Revenko, V.S. Pakhopol, K.M. Indrichan, Zh. Obshch. Khim., 59, 1713 (1989);
104. Chem. Abstr. 112, 47562f (1989).
105. A.O. Abdelhamid, S.E. Abdou. Sulfur Lett., 6, 41 (1987).
106. H.F. Zohdi, N.M. Rateb, A.O. Abdelhamid. Phosphorus, Sulfur & Silicon, 133, 103 (1998).
107. A.S. Shawali, M.A. Abdallah, M.E.M. Zayed. Z. Naturforsch, 55b, 546 (2000).
108. A.O. Abdelhamid, S.M. Al-Shehri. J. Chem. Res. (S), 240, (M) 1681 (1997).
109. A.M. Farag, K.M. Dawood, Z.E. Kandeel. Tetrahedron, 53, 161 (1997).
110. R. Huisgen, R. Grashey, M. Seidel, H. Knupfer, R. Schmidt. Ann. Chem., 65B, 169 (1962).
111. A.A. Fahmi, H.A. Abdelhadi, M.S. Algharib. Phosphorus, Sulfur & Silicon, 105, 163 (1995).
112. A.O. Abdelhamid, N.H. Metwally, N.H. Bishai. J. Chem. Res. (S), 462, (M) 1144 (2000).
113. M.L. Petrov, M.A. Abramov. Phosphorus, Sulfur & Silicon, 134/135, 331 (1998).
114. T.A. Abdallah, H.A. Abdelhadi, H.M. Hassaneen. Phosphorus, Sulfur & Silicon, 177, 59 (2002).
115. A.O. Abdelhamid, N.A. Abdelreheem, N.M. Hassan. Heteroat. Chem., 11, 213 (2000).
116. L.S. Pupko, A.I. Dychenko, P.S. Pelkis. Ukr. Khim. Zh., 38, 1049 (1972);
117. Chem. Abstr., 78, 29686z (1973).
118. R.J. Bochis, A. Kotliar, W.H. Parsons, K. Rupprecht. PCT Int. Appl. WO, 25,936 (1996); Chem. Abstr., 125, 275896s (1996).
119. R. Norton, M.K.A. Ibraham. U.S. US 5,506,228 (1996); Chem. Abstr., 125, P3363w (1996).
120. H. Hamberger, H. Reinshagen, G. Schulz, G. Sigmund. Tetrahedron Lett., 41, 3619 (1977).
121. H. Neunhoeffer, H. Hammann. Liebigs Ann. Chem. 283 (1984).
122. N.M. Elwan, A.A. Fahmy, T.A. Abdallah, H.M. Hassaneen. Sulfur Lett., 18, 9 (1994).
123. M.H. Elnagdi, M.R.H. Elmoghayar, E.M. Kandeel, M.K.A. Ibrahim. J. Heterocycl. Chem., 14, 227 (1977).
124. M.H. Elnagdi, M.R.H. Elmoghayar, H.A. Elfahham, H.H. Alnima. J. Heterocycl. Chem., 17, 209 (1980).
125. A.S. Shawali, A.H. Elghandour, A.R. Sayed. Synth. Commun., 31, 731 (2001).
126. A.S. Shawali, M.A. Abdallah, M.A.N. Mosselhi, T.A. Farghaly. Heteroat. Chem., 13, 136 (2002).
127. M.A.N. Mosselhi. Monatsh. Chem., 133, 1297 (2002).
128. H.M. Hassaneen, H.A. Abdelhadi, T.A. Abdallah. Tetrahedron. 57, 10133 (2001).
129. N.M. Elwan, E.M. Awad, H.M. Hassaneen, A. Linden, Heimgartner. Helv. Chim. Acta, 86, 739 (2003).
130. A.A. Fahmi, M.S. Algharib. Egypt. J. Pharm. Sci., 4, 267 (1995).
131. A.S. Shawali, M.A. Abdallah, M.A.N. Mosselhi, Y.F. Mohamed. Z. Naturforsch., 57b, 552 (2002).
132. D.J. Collins, T.C. Hughes, W.M. Johnson. Aust. J. Chem., 53, 137 (2000).
133. M. ElMessaoudi, A. Hasnaoui, M. ElMohtadi, J.P. Lavergne. Bull. Soc. Chem. Belg., 10, 977 (1992).
134. A.O. Abdelhamid, S.S. Ghabrial, M.Y. Zaki, N.A. Ramadan. Arch. Pharm. (W), 325, 205 (1992).
135. P. Frohberg, M. Wiese, P. Nuhn. Arch. Pharm. Pharm. Med. Chem., 330, 47 (1997).
136. P. Frohberg, U. Baumeister, D. Strohl, H. Danz. Heterocycles, 45, 1183 (1997).
137. C. Parkanyi, A.O. Abdelhamid, A.S. Shawali. J. Heterocycl. Chem., 21, 521 (1984).
138. D.E. Ames, S. Chandrasekhar, K.J. Hansen. J. Chem. Soc. Perekin Trans. 1, 539 (1978).
139. A.S. Shawali, M.A. Abdallah, M.M. Zayed. J. Heterocycl. Chem., 39, 45 (2002).
140. A.S. Shawali, S.M. Elsheikh. J. Prakt. Chem., 342, 96 (2000).
141. N.M. Hassan, A.O. Abdelhamid. J. Chem. Res. (S) 350, (M) 2244 (1997).
142. A.S. Shawali, M.A.N. Mosselhi, N.M. Tawfik. J. Org. Chem., 66, 4055 (2001).
143. H.A. Abdelhadi, T.A. Abdallah, H.M. Hassaneen. Heterocycles, 41, 1999 (1995).
144. A.S. Shawali, R.H. Hilal, S.M. Elsheikh. Montasch, Chem., 132, 715 (2001).
145. H.M. Hassaneen, T.A. Abdallah. Molecules, 8, 333 (2003).
146. T.A. Abdallah, M.A. Darwish, H.M. Hassaneen. Molecules, 7, 494 (2002).
147. M.A. Abdallah. Montasch. Chem., 132, 959 (2001).
148. E. Rakib, M. Benchidmi, E. Essassi, A. ElBouadili, M. Khouli, J.M. Barbe, M.D. Pujol. Heterocycles, 53, 571 (2000).
149. H.M. Hassaneen, T.A. Abdallah, H.A. Abdelhadi, H.M.E. Hassaneen, R.M. Pagni. Heteroat. Chem., 14, 491 (2003).
150. N.V. Gerbeleu, A.A. Dobrov, Yu.A. Simonov, V.E. Zavodnik, T.I. Malinovskii. Zh. Neorg. Khim., 38, 486 (1993),
151. CA 119, 172927z (1993).
152. Y. Singh, R. Sharma, R.N. Kapoor. Transition Met. Chem. (Weinheim), 11, 321 (1986).
153. F.H. Herbstein, W. Schwotzer. J. Chem. Soc. Perkin Trans. 2, 1917 (1984).
154. S. Trotto, J.A. Furch, D.G. Kuhn, D.A. Hunt. Eur. Pat. Appl. EP, 709,372 (1996); Chem. Abstr., 125, 58090v (1996).
155. W.K. Kitagawa, K. Wada, Y. Ito, Y. Otsu, Y. Hattori, K. Shibuya, T. Abe. Jpn K.T. K. JP 10,237,040 (1998); Chem. Abstr., 129, 244922a (1998).
156. R.E. Diehl, D.A. Hunt, S.H. Trotto. US 6,242,647 (2001); Chem. Abstr., 135, 19448e (2001).
157. A.N. Krasovskii, A.K. Bulgakov, A.P. Andrushko, I.A. Krasovskii, A.M. Dyachenko, A.A. Bokun, N.A. Kravchenko, A.M. Demchenko. Pharm. Chem. J., 34, 115 (2000).
158. G.G. Davidyan, L.T. Rumyantseva, E.P. Nesynov. Fiziol. Akt. Veshchestva, 8, 68 (1976);
159. Chem. Abstr., 87, 1047d (1977).
160. Y. Takezawa, Jpn. K.T.K. JP 04,330,052 (1992), Chem. Abstr., 119, 237919v (1993).
161. Y. Zeng, C. Tang, G. Shen, R. Yu. Huaxue Chuanganqi, 19, 18 (1999);
162. Chem. Abstr., 131, 294932r (1999).
163. Y. Zeng, C. Tang, G. Shen, R. Yu. Huaxue Chuanganqi, 18, 26 (1998);
164. Chem. Abstr., 130, 275958s (1999).
165. S. Tian. Guilin Yejin Dizhi Xueyuan Xuebao, 14, 420 (1994);
166. Chem. Abstr., 122, 273573y (1995).
167. A.V. Kotov, I.Yu. Davydova, N.M. Golovkina. Zh. Anal. Khim., 37, 594 (1982);
168. Chem. Abstr., 97, 65557j (1982).
169. A.V. Kotov, I.Yu. Davydova, N.M. Golovkina. USSR SU 975707 (1982), Chem. Abstr., 98, 172226t (1983).