Synthesis of phosphonyl 1,2,3-thiadiazoles
Hu Chen
National Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China
Search for more papers by this authorWen-Hu Wang
National Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China
Search for more papers by this authorMei Xue
National Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China
Search for more papers by this authorRu-Zhen Cao
National Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China
Search for more papers by this authorCorresponding Author
Lun-Zu Liu
National Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China
National Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. ChinaSearch for more papers by this authorHu Chen
National Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China
Search for more papers by this authorWen-Hu Wang
National Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China
Search for more papers by this authorMei Xue
National Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China
Search for more papers by this authorRu-Zhen Cao
National Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China
Search for more papers by this authorCorresponding Author
Lun-Zu Liu
National Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China
National Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. ChinaSearch for more papers by this authorAbstract
In accord with the Hurd-Mori reaction conditions, 1- or 2-phosphonyl hydrazones reacted with thionyl chloride to afford 4- or 5-phosphonyl 1,2,3-thiadiazoles in good yields and purity. A synthesis of 1- or 2-phosphonyl hydrazones using two methods is described. © 2000 John Wiley & Sons, Inc. Heteroatom Chem 16:413–416, 2000
REFERENCES
- 1 Krueger, H.; Arndt, F.; Rush, R.; Schering A. G.; Ger Patent DE 3139505, 1983; Chem Abstr 1983, 99, 53761z.
- 2 Kuebel, B.; Knauf, W.; Sachse, B.; Walterdorfer, A.; Hiechst A. G.; Ger Patent DE 3203656, 1983; Chem Abstr 1984, 100, 139338t.
- 3"> Tsubata, K.; Shimaoka, T.; Takagi, K.; Baba, K.; Tajima, S. (Nihon Nohayku Co., Ltd.), PCT Int Appl WO 9814438, 1996; Chem Abstr 1998, 128, 257437a.
- 4 Korobi, T.; Hiraga, T.; Fujita, M.; Kondo, S.; Asada, T.; Tsuboi, H. (Zaidan Hojin Sagami Chemical Research Center) Jpn. Kokai Tokkyo Koho JP 249665, 1997; Chem Abstr 1997, 127, 278196r.
- 5 Fuji, K.; Hatano, K.; Narita, I.; Shikida, S.; Tanaka, T.; Nakamoto, Y. (Ube Industries, Ltd.) Jpn Kokai Tokkyo Koho JP 287659, 1998; Chem Abstr 1998, 129, 330735y.
- 6 Yamaguti, M.; Onishi, M.; Nishida, T.; Morimoto, M.; Sakata, K.; Tsubata, K. (Nihon Nohyaku Co., Ltd.) PCT Int Appl WO 52882, 1999; Chem Abstr 1999, 131, 271880h.
- 7 Khokhlov, P. S.; Kashemirov, B. A.; Mikityuk, D.; Strepikheev, Yu. A.; Chimishkyan, A. L. Zh Obshch Khim 1984, 54 (11), 2641–2642; Chem Abstr 1985, 102, 166869z.
- 8 Hurd, C. D.; Mori, R. I. J Am Chem Soc 1955, 77, 5359–5364.
- 9 Fujita, M.; Kobori, T.; Hiyama, T.; Kondo, K. Heterocycles 1993, 36 (1), 33–36.
- 10 Kaushik, M. P.; Lal, B.; Raghuveeran, C. D.; Vaidyanathaswamy, R. J Org Chem 1982, 47, 3503–3505.
- 11 Corbel, B.; Medinger, L.; Haelters, J. P.; Sturtz, G. Synthesis 1985, 1048–1051.
- 12 Edmundron, R. S. Dictionary of Organophosphorus Compounds; Chapman and Hall: New York, 1987; p 806.
- 13 Darrell, B. K.; Hellwege, D. M.; Nagabhushanam, M. J Org Chem 1965, 30, 1265–1267.
- 14 Takamizawa, A.; Sato, H. Chem Pharm Bull 1975, 23 (5), 948–954.
- 15 Liorber, B. G.; Tarzivolova, T. A.; Pavlov, V. A.; Zykova, T. V.; Kisilov, V. V.; Tuamsheva, N. A.; Suzkii, A. Yu.; Shagvaleev, F. Sh. Zh Obshch Khim 1987, 57, 534–538; Chem Abstr 1988, 108, 167566z.
- 16 Razumov, A. I.; Moskva, V. V. Zh Obshch Khim 1964, 34 (8), 2589–2594; Chem Abstr 1964, 61, 14707a.
- 17 Cotton, F. A.; Schunn, R. A. J Am Chem Soc 1963, 85, 2394–2402.
- 18 Mathey, F.; Savignac, P. Tetrahedron 1978, 34, 649–654.
- 19 Krueger, H.; Schering A. G.; Ger Patent 2636994, 1978; Chem Abstr 1978, 88, 152630k.
- 20 Modarai, B.; Ghandehari, M. H.; Massoumi, H. J Heterocyc Chem 1974, 11 (3), 343–345.
