Pyran-2-ones as a versatile synthon for the synthesis of diverse arenes and heteroarenes

Current Organic Chemistry

Volumn 5, Issue 5, 2001, Pages 571-599

  Ram, Vishnu Ji ^a   Srivastava, Pratibha ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

PHOTOCHEMICAL REACTIONS;

HETEROARENES; NUCLEOPHILIC CENTERS; ORGANICS; PHOTOCHEMICAL TRANSFORMATIONS; PHOTOCHEMICALS; PYRAN-2-ONES; RING TRANSFORMATION; STRUCTURAL FEATURE; SYNTHONS; TRANSFORMATION REACTIONS;

SUBSTITUTION REACTIONS;

2 PYRONE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG SYNTHESIS; DRUG TRANSFORMATION; ELECTROPHORESIS; MOLECULAR INTERACTION; PHOTOCHEMISTRY; REACTION ANALYSIS; REVIEW; STRUCTURE ANALYSIS;

EID: 0035018440     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272013375454     Document Type: Review

References (183)

1. Mors, W.B., Gottlieb, O.R., Djerassi, C. J. Am. Chem. Soc., 1957, 79, 4507.
2. Gottlieb, O.R., Mors, W.B. J. Org. Chem., 1959, 24, 17.
3. Kretzschmar, R., Meyer, H..J., Teschendorf, H.J., Zoellner, B. Arch. Int. Pharmacodyn. Ther. 1969, 180, 475; [Chem. Abstr., 1970, 72, 20254a].
4. Kretzschmar, R., Meyer, H..J., Teschendorf, H.J., Zoellner, B. Arch. Int. Pharmacodyn. Ther. 1969, 180, 475; [Chem. Abstr., 1970, 72, 20254a].
5. McGahren, W.J., Ellestad, G.A., Morton, G.O., Kunstman, M.P., Mullen, P. J. Org. Chem., 1973, 38, 3542.
6. Yamazaki, M., Maebayashi, Y., Katoh, H., Ohishi, J., Koyama, Y. Chem. Pharm. Bull, 1975, 23, 569.
7. Talapatra, B., Pradhan, D.K., Talapatra, S.K. Indian J. Chem., 1976, 14B, 300.
8. Camarda, L., Merlini, L., Nasini, G. Phytochemistry, 1976,15, 537.
9. Priestap, H.A., Bonafede, J.D., Ruveda, E.A. Phytochemistry, 1977, 16, 1578.
10. Shimizu, S., Sakurai, I., Yamamoto, Y. Chem. Pharm. Bull., 1983, 31, 3781.
11. Vishwakarma, R.A., Kapil, R.S., Popli, S.P. Indian J. Chem., 1983, 22B, 612.
12. Bevalot, F., Fournet, A., Moretti, C., Vaquette, J., Waterman, P.G., Young, S.A. Phytochemistry, 1983, 22, 2875.
13. Irschik, H., Gerth, K., Hofle, G., Kohl, W., Reichenbach, H. J. Antibiotics, 1983, 36, 1651.
14. Shizuri, Y., Kosemura, S., Yamamura, S., Furukawa, H., Kawai, K., Okada, N. Tetrahedron Letts., 1984, 25, 1583.
15. Sparace, S.A., Mudd, J.B., Bruke, B.A., Aasan, A.J. Phytochemistry, 1984, 23, 2693.
16. Spencer, G.F., England, R.E., Wolf, R.B. Phytochemistry, 1984, 23, 2499.
17. Hiraoka, H., Furuta, K., Ikeda, N., Yamamoto, H. Bull. Chem. Soc. Jpn., 1984, 57, 2777.
18. Mori, K., Otsuka, T., Oda, M. Tetrahedron Letts., 1984, 40, 2929.
19. Kikukawa, T., Tai, A. Chem. Letts., 1984, 1935.
20. Capon, R.J., Faulkner, D.J. J. Org. Chem., 1984, 45, 2506.
21. Ichihara, A., Murakami, K., Sakamura, S. Tetrahedron, 1987, 43, 5245.
22. Tal, B., Robeson, D.J., Burk, B.A., Aasen, A.J. Phytochemistry, 1985, 24, 729.
23. Tadano, K., Ueno, Y., Ogawa, S. Chem. Letts., 1988, 111.
24. Sugawara, Y., Kawai, H., Matsumoto, T., Okano, K., Takizawa, S. PCT. Int. Appl. WO 9916763/1999; Chem. Abstr., 1999, 130, 281990n.
25. Prasad, J. V. N., Pavolovsky, P., Para, K. S., Ellsworth, E. L., Tummino, P. J., Nouhan, C., Ferguson, D. Bio. org. Med. Chem. Letts., 1996, 6, 1113.
26. Prasad, J.V. N., Para, K. S., Lunney, E. A., Ortwine, D. E., Dunbar, J. B. Jr., Ferguson, D., Tummino, P. J., Hupe, D., Bradley, B. D., J. Am. Chem. Soc., 1994, 116, 6989.
27. Tawata, S., Atariyama, S., Kohamoto, N., Jpn. Kokai. Tokkyo. Koho., JP 09328493/1997; Chem. Abstr., 1998, 128, 48369.
28. Yamauchi, T., Nakashino, S., Hirayama, M., Ojiri, K., Suda, K., Jpn. Kokai. Tokkyo. Koho., JP 10101663/1998;Chem. Abstr., 1998, 129, 3907u.
29. Takeno, S., Okwa, H., Nishijawa, M., Kanazawa, T., Hasata, T., Minobe, Y. Jpn. Kokai. Tokkyo. Koho. JP 10182626/1998; Chem. Abstr., 1998,129, 144867t.
30. Ellsworth, E.L., Lunney, E., Tait, B. D., US. US 5789440/1998; Chem. Abstr., 1998,129, 161492j.
31. Demagala, J.M., Ellsworth, E. L., Lunney, E., Ortwine, D. F., Para, K. S., Prasad, J.V. N., T., Tait, B. D. US. US 5808062/1998; Chem. Abstr, 1998, 129, 245043b.
32. de Mayo, P., Yip, R.W. Proc. Chem. Soc., 1964, 84.
33. Corey, E.J., Streith, J. J. Am. Chem. Soc., 1964, 86, 950.
34. Padwa, A., Hartman, R. Ibid, 1966, 88, 1518.
35. de Mayo, P.; Advan. Org. Chem., 1960, 2, 394.
36. Gompper, R., Christman, O. Chem. Ber., 1961, 94, 1784.
37. Bland, N., Thorpe, J.F. J. Chem. Soc., 1912, 101, 1557.
38. Vogel, G. J. Org. Chem., 1965, 30, 203.
39. Diels, O., Alder, K. Ann., 1931, 490, 257.
40. Zimmerman, H.E., Paufler, R.M. J. Am. Chem. Soc., 1960, 82, 1514.
41. Evnin, A.B., Seyferth, D. Ibid, 1967, 89, 952.
42. Pirkle, W.H., Dines, M. J. Org. Chem., 1969, 34, 2239.
43. Shusherina, N.P., Dmitrieva, N.D., Kozlova, T.F., Levina, R.Y. Zhur. Obshch. Khim., 1960, 30, 2829.
44. Shusherina, N.P., Dmitrieva, N.D., Levina, R.V. Ibid, 1961, 31, 2794.
45. Shusherina, N.P., Dmitrieva, N.D., Levina, R.Y. Dokl. Akad. Nauk. SSSR, 1960, 135, 1406.
46. Feist, F. Ber., 1893, 26, 747.
47. Feist, F. Ibid, 1901, 34, 1996.
48. Katritzky, A.R., Ambler, A.P. in "Physical Methods in Heterocycl. Chemistry," ed. A.R. Katritzky, Academic Press, New York, 1963, 2, 252.
49. Fried, J., Elderfield, R.C. J. Org. Chem., 1941, 6, 566.
50. Pirkle, W.H., Dines, M. J. Heterocycl. Chem., 1969, 6, 1.
51. Pirkle, W.H., Dines, M. J. Heterocycl. Chem., 1969, 6, 313.
52. Sibs, S. Tetrahedron, 1975, 31, 2229.
53. Griffin, D.A., Stauton, J. J. Chem. Soc. Chem. Comm., 1975, 675.
54. Shusherina, N.P., Dmitrieva, N.D., Levina, R.Y. Zhur. Obschei. Khim., 1961, 31, 2794.
55. Pirkle, W.H., Dines, M. J. Org. Chem., 1969, 34, 2239.
56. Bu'Lock, J.D., Smith, H.G. J. Chem. Soc., 1960, 502.
57. Arndt, F., in "Organic Synthesis," ed. C.F.H. Allen, Wiley, New York, 1940, 26.
58. Anker, R.M., Cook, A.H. J. Chem. Soc., 1945, 311.
59. Buchner, E., Schröder, H. Ber., 1902, 35, 782.
60. Wiley, R.H., Smith, N.R. Organic Synthesis., 1951, 31, 23.
61. Harris, T.M., Harris, C.M., Hindley, K.B. Fortsch. Chem. Org. Naturstoffe., 1974, 217.
62. a) Huckin, S.N., Weiler, L. Tetrahedron Letts., 1972, 2405.
63. b) Harris, T.M., Harris, C.M. J. Org. Chem., 1966, 31, 1032.
64. Gogte, G.R. Proc. Indian Acd. Sci, 1938, 7A, 214.
65. Effenberger, F., Ziegler, T., Schönwälder, K.H., Kesmarszky, T., Bauer, B. Chem., Ber., 1986, 119, 3394.
66. Tanyeli, C., Demir, A.S., Özarslan, Ö, Mecidoglu, I., Tarhan, O. Heterocycles, 1994, 37, 1705.
67. Toplak, R., Selic, L., Sorsak, G., Stanovnik, B. Heterocycles, 1997, 45, 555.
68. a) Andreichikov, Yu. S., Nalimova, Yu.A., Plakhina, G.D., Saraeva, R.F., Tendryakova, S.P. Khim. Gete.. Soedln., 1975, 1468; [Chem. Abstr., 1976, 84, 74222].
69. a) Andreichikov, Yu. S., Nalimova, Yu.A., Plakhina, G.D., Saraeva, R.F., Tendryakova, S.P. Khim. Gete.. Soedln., 1975, 1468; [Chem. Abstr., 1976, 84, 74222].
70. b) Y.S. Andreichikov, U.A. Nalimova, A.P. Kozlov, I.A. Rusakov; J. Org. Chem. USSR, 1978, 14, 2245.
71. Fuson, R., Little, J., Miller, G. J. Am. Chem. Soc., 1938, 60, 2404.
72. Buchner, E., Schroder, H. Ber., 1902, 35, 782.
73. Tominaga, Y. Trends in Heterocyclic Chemistry, 1991, 2, 43.
74. Tominaga, Y., Ushirogouchi, A., Matsuda, Y., Kobayashi, G. Chem. Pharm. Bull., 1984, 32, 3384.
75. Tominaga, Y., Ushirogouchi, A., Matsuda, Y. J. Heterocycl. Chem., 1987, 24, 1557.
76. Mingo, P., Zhang, S., L. Liesbeskind, S., J. Org. Chem., 1999, 64, 2145.
77. Roses, N., Salmon, M., Sharma, P., Alvarez, C., Ramirez, R., Garcia, J. L., Arzoumanian, H., J. Chem. Soc. Perkin. Trans. 1, 2000, 1493.
78. Dare, D. L., Entwistle, I.D., Johnstone, R.A.W.; J. Chem. Soc. Perkin. Trans, 1, 1973, 1130.
79. Shusherina, N.P., Demitrieva, N.D., Luk'yanets, E.A., Levina, R.Y. Zh. Org. Khim., 1963, 38, 3434.
80. Robertson, D.N., Link, K.P. J. Am. Chem. Soc., 1953, 75, 1647.
81. Kvita, V., Fischer, W. Chimia., 1992, 46, 457.
82. Posner, G.H., Harrison, W., Wettlaufer, D.G. J. Org. Chem., 1985, 50, 5041.
83. Kvita, V., Sauter, Hp., Unveröffentlichte Er-gebniss; Chimia, 1992, 46, 457.
84. Kvita, V., Saulter, Hp. Helv. Chim. Acta., 1990, 73, 883.
85. Wiley, R.H., Slaymaker, S.C. J. Am. Chem. Soc., 1956, 78, 2393.
86. Oikawa, H., Kobayashi, T., Katayama, K., Suzuki, Y., Ichihara, A. J. Org. Chem., 1998, 63, 8748.
87. Vogel, G. Chem. Ind. (London), 1962, 968, 1829.
88. Gompper, R., Christmann, O. Chem. Ber., 1961, 94, 1796.
89. Freed, J., Elderfield, R.C. J. Org. Chem., 1941, 6, 577.
90. Junek, H., Wilfinger, W. Monotsh Chem., 1970, 101, 1123.
91. Vogel, G. J. Org. Chem., 1965, 30, 203.
92. Ram, V.J., Verma, M. Indian J. Chem., 1990, 29B, 624.
93. Van Dam, M.J.D., Kögl, F. Reac. Trav. Chem., 1964, 83, 39.
94. Tominaga, Y., Ushirogochi, A., Matsuda, Y. J.Heterocycl. Chem., 1987, 24, 1557.
95. Ram, V.J., Haque, N., Nath, M., Singh, S.K., Hussaini, F.A., Tripathi, S.C., Patnaik, G.K., Shoeb, A. Med. Chem. Letts, 1997, 7, 3149.
96. Bisagni, E., Civier, A., Marquet, J.P. J. Heterocycl. Chem., 1975, 12, 461.
97. Glombick, H., Tochtermann, W. Chem. Ber., 1983, 116, 3366.
98. Ram, V.J., Haque, N., Singh, S.K., Hussaini, F.A., Shoeb, A. Indian J. Chem., 1993, 32B, 924.
99. Ram, V.J., F.A. Hussaini, S.K. Singh, A. Shoeb; J. Chem. Res(S), 1993, 110.
100. Ram, V.J., Goel, A., Shukla, P.K., Kapil, A. Bioorg. Med. Chem. Letts., 1997, 7, 3101.
101. Minunni, G. Gazz. Chim. Ital., 1899, 29, 456.
102. Marcus, E., Chan, J.K., Hughes, J.L. J. Chem. Eng. Data., 1967, 12, 151.
103. Kato, T., Kawamata, J, Shibata, T. Yakugaku Zasshi, 1968, 88, 106.
104. Saalfrank, R.W., Gündel, J., Rossmann, G., Hanek, M., Rost, W., Peters, K., Vonschnering, H.G. Chem. Ber., 1990, 123, 1175.
105. Marquet, J., Moreno-Manas, M. Chem. Letts., 1981, 173.
106. Ram, V.J. Unpublished work.
107. Mareno-Manas, M., Ribas, J., Virgili, A. Synthesis, 1985, 699.
108. Hagiwara, H., Miya, S., Suzuki, T., Ando, M., Yamamoto, I., Kato, M. Heterocycles, 1999, 51, 493.
109. Scott, A.I., Guilford, H, Skingle, D. Tetrahedron, 1971, 27, 3039.
110. Wolfbeis, O.S., Ziegler, E., Knierzinger, A., Wipfler, H., Trummer, I. Monatsch Chem., 1980, 111, 93.
111. Hormi, O.E.O., Paakkanen, A.M. J. Org. Chem., 1987, 52, 5275.
112. Caputo, O., Cattel, L., Ceruti, A., Rua, G. Ann. Chim., 1974, 64, 685.
113. Bravo, P., Frigerio, M., Ticozzi, C. J. Heterocycl. Chim., 1988, 25, 647.
114. Strakov, A.Y., Sulca, M., Egle, A., Mols, A. Latv. PSR Zinat. Akad Vestis. Kim. Sir., 1970, 615; [Chem. Abstr., 1971, 74, 53423].
115. Strakov, A.Y., Sulca, M., Egle, A., Mols, A. Latv. PSR Zinat. Akad Vestis. Kim. Sir., 1970, 615; [Chem. Abstr., 1971, 74, 53423].
116. Azuma, Y., Sato, A., Morone, M., Heterocycles, 1993, 35, 599.
117. Orchin, M., Woolfolk, E.O. J. Am. Chem. Soc., 1945, 67, 122.
118. Rabideau, P.W., Harvey, R.G. J. Org. Chem., 1970, 35, 25.
119. Rabideau, P.W., Marcinow, Z. Tetrahedron Letts., 1988, 29, 3761.
120. Erdhman, H., Ronlan, A. Acta. Chem. Scand., 1969, 23, 249.
121. Ram, V.J., Goel, A. Tetrahedron Letts., 1996, 37, 93.
122. Goel, A., Srivastava, P., Nath, M., Ram, V.J. Synthesis., 1998, 167.
123. Ram, V.J., Goel, A. J. Chem. Res., 1997, 640.
124. Ram, V.J., Goel, A. Synthesis, 1999, 467.
125. Ram, V.J., Goel, A. Chem. Letts., 1997, 1021.
126. Ram, V.J., Goel, A. J. Org. Chem., 1999, 64, 2387.
127. Math, M., Srivastava, P., Goel, A., Ram, V. J. Eur. J. Org. Chem., 1998, 2083.
128. Ram, V.J., Srivastava, P., M. Nath; Synthesis, 1999, 1884.
129. Ram, V.J., Srivastava, P. Communicated in Synlett.
130. Griffin, D.A., Staunton, J. J. Chem. Soc. Chem. Comm., 1975, 675.
131. Money, T. Chem. Rev., 1970, 70, 553.
132. Shusherina, N.P., Laptova, V.L. J. Org. Chem. USSR (Eng. Transl), 1974, 10, 852.
133. Peyman, A., Reusching, D. B., Linkies, A. H. Eur. Pat. Appl. EP 710650/1996; Chem. Abstr., 1996, 125, 58332a.
134. Rosenstock, B., Peyman, A., Ruppert, D., Riess, G., PCT. Int. Appl. WO 9630342/1996; Chem. Abstr., 1997, 126, 7993c.
135. Lassalle, G., Bellevergue, P., Bourbier, J. C., Galtier, D., Martin, V. Fr. Demande FR 2758326/1998; Chem. Abstr., 1998, 129, 175556v.
136. Ram, V.J., Verma, M., Hussaini, F.A., Shoeb, A. Liebigs Ann. Chem., 1991, 1229.
137. Hussaini, F.A., Pragya, Ram, V. J., Singh, S.K., Nath, M., Shoeb, A., Bhaduri, A.P. J. Chem. Res.,(S), 1994, 86.
138. Ram, V.J., Mumtazuddin, S., Pragya, Haque, N., Hussaini, F.A., Shoeb, A., Bhaduri, A.P. J. Chem. Res(S), 1994, 354.
139. Ram, V. J., Srivastava, P., Communicated in Synthesis.
140. Kohly, I. El-S. El., Mishrikey, M.M., Fuid-Alla, H.M. J. Heterocycl. Chem., 1975, 12, 129.
141. Jones, R. C. F., Bhaley, G., Patience, J. M., Patel, P., J. Chem. Res., 1999, 4, 250.
142. Hubert-Habart, M., Pene, C., Royer, R. Chim. Ther., 1973, 8, 314.
143. Tagaki, K., Hubert-Habart, M. Bull. Soc. Chim. France., 1977, 369.
144. Cram, D.J., Tanner, M.E., Thomas, R. AG (E) 1991, 30, 1024.
145. Chapman, O.L, McIntosh, Pacnsky, C.L. J. Am. Chem. Soc., 1973, 95, 614.
146. Lin, C.Y., Krantz, A. Chem. Comn., 1972, 111.
147. McIntosh, C.L., Chapman, O.L. J. Am. Chem. Soc., 1973, 95, 247.
148. Bedford, C.T., Forrester, J.M., Money, T. Canad. J. Chem., 1970, 48, 2645.
149. Staunton, J. Comprehensive organic chemistry; The synthesis, Reactions of organic compounds; Sir Derek Barton, W.D. Ollis Vol. 4.
150. de Mayo, P., Yip, R.W. Proc. Chem. Soc., 1964, 84.
151. Van Meerbeck, M., Toppet, S., de Schryver, F.C.; Tetrahedron Letts., 1972, 2247.
152. Adam, W., Erden, I. J. Am. Chem. Soc., 1979, 101, 5692.
153. Gomez, A. M., Mantecon, S., Valverde, S., Lopez, J. C. J. Org. Chem., 1997, 62, 6612.
154. Woodard, B. T., Posner, G. H. Adv-cycloaddition, 1999, 5, 47; Chem. Abstr., 1999, 131, 18884z.
155. Woodard, B. T., Posner, G. H. Adv-cycloaddition, 1999, 5, 47; Chem. Abstr., 1999, 131, 18884z.
156. Diels, O., Alder, K. Ann., 1931, 490, 257.
157. Shusherina, N.P., Russ. Chem. Rev., 1974, 43, 851.
158. Seyferth, D., White, D.L. J. Organometalic. Chem., 1972, 34, 119.
159. Sakurai, H., Nakadaria, Y., Hosomi, A., Eriyama, Y. Chem. Letts., 1982, 1971.
160. Sakurai, H., Eriyama, Y., Hosomi, A., Nakadaria, Y., Kaputa, C. Chem. Letts., 1984, 595.
161. Market, G., Gin, G.Y., Silbereisen, E. Angew. Chem. Int. Ed. Engl.,1982, 21, 370.
162. Caino, P., Echavarren, A., Prados, P., Farina, F. J. Org. Chem., 1983, 48, 5373.
163. Gingrich, H.L., Roush, D.M., Van Saun, W.A. J. Org. Chem., 1983, 48, 4869.
164. Neidlein, R., Kohl, M., Kramer, W. Helv. Chim. Acta., 1989, 72, 1311.
165. Feiser, L.F., Haddadin, M.J. J. Am. Chem. Soc., 1964, 86, 2081.
166. Kende, A.S., Curran, D.P., Tsay, Y.G., Mills, J.E. Tetrahedron Letts., 1977, 3537.
167. Mehta, G., Venkateswarlu, Y. J. Chem. Soc. Chem. Commun., 1988, 1200.
168. Tamura, Y., Fukata, F., Tsugoshi, T., Sasho, M., Nakajima, Y., Kita, Y.K. Chem. Pharm. Bull, 1984, 32, 3259.
169. Shino, T., Yamasaki, S., Date, K., Uemura, H., Somekawa, K., J. Heterocycl. Chem., 1993, 30, 419.
170. Trost, P.B.M., Schneider, S. Angew. Chem., Int. Et. Engl., 1989, 28, 213.
171. Hongm , B. C., Sun, S. S., Chem. Commun., 1996, 8, 937.
172. Low, W., Braun, B., Muller, B., J. Heterocycl. Chem., 1994, 31, 1577.
173. Rafiuddin, M. R., Siddiqui, Z. S., Zaman, A., Chowdhary, A. R., Mohammed, I., Indian. J. Chem., Sect B., 1994, 33, 1023.
174. Isomura, Y., Yamasaki, S., Okada, H., Naguchi, M., Heterocycl. Commun., 1995,1, 421.
175. Voss, E., Reiter, R., Kilpert, C. Ger Offen. DE 4332203/1995; Chem. Abstr., 1995, 123, 32860e.
176. Udden, R., Zaman, A, Indian J. Chem., Sect B. 1995, 34, 639.
177. Azuma, Y., Sato, A., Morone, M.; Ann. Rep.Thoku. Coll. Pharm., 1992, 39, 251; Chem. Abstr., 1994, 121, 82955u.
178. Azuma, Y., Sato, A., Morone, M.; Ann. Rep.Thoku. Coll. Pharm., 1992, 39, 251; Chem. Abstr., 1994, 121, 82955u.
179. Azuma, Y., Sato, A., Morone, M.; Heterocycle., 1995, 38, 1574.
180. Despande, V. H., Khan, R. A., Rai, B., Ayyangar, N. R. Synth. Commun. 1993, 23, 2337. Chem. Abstr., 1994, 120, 163777a.
181. Despande, V. H., Khan, R. A., Rai, B., Ayyangar, N. R. Synth. Commun. 1993, 23, 2337. Chem. Abstr., 1994, 120, 163777a.
182. Susnik, I., Vorkapic-Furac, Durakovic, J. S., Koprivanac, S., Lasinger, J. Monatsh Chem, 1992, 123, 817; Chem. Abstr.,1993, 118, 147430d.
183. Susnik, I., Vorkapic-Furac, Durakovic, J. S., Koprivanac, S., Lasinger, J. Monatsh Chem, 1992, 123, 817; Chem. Abstr.,1993, 118, 147430d.