Regioselective cyclocondensations of chlorocarbonylsulfenyl chloride with hydrazones: Effective synthesis of a class of sulfur and nitrogen containing heterocycles with -cos- linkage

Heterocycles

Volumn 43, Issue 1, 1996, Pages 141-149

  Tanabe, Yoo ^a   Mori, Kei ^a   Nishii, Yoshinori ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0345442260     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-95-7242     Document Type: Article

References (22)

1. N. H. Dhar and K. S. K. Murthy, Synthesis, 1986, 437; A. Kamal and P. B. Sattur, Heterocycles, 1987, 26, 1051.
2. N. H. Dhar and K. S. K. Murthy, Synthesis, 1986, 437; A. Kamal and P. B. Sattur, Heterocycles, 1987, 26, 1051.
3. 2O in a large scale: E. Muehlbauer and W. Weiss, German Pat. 1233882 (Chem. Abstr., 1967, 66, 95023j). As for applications of 1: K. Pilgram and R. D. Skiles, J. Org. Chem., 1973, 38, 1578; D. Baldwin and P. Van den Broek, J. Chem. Soc., Perkin Trans. 1, 1975, 375; R. K. Howe, T. A. Gruner, and J. E. Franz, J. Org. Chem., 1977, 42, 1813; J. Goerdeler and K. Nandi, Chem. Ber., 1981, 114, 549; S. Kabashima, T. Okawara, T. Yamasaki, and M. Furukawa, J. Heterocycl. Chem., 1991, 28, 1957.
4. 2O in a large scale: E. Muehlbauer and W. Weiss, German Pat. 1233882 (Chem. Abstr., 1967, 66, 95023j). As for applications of 1: K. Pilgram and R. D. Skiles, J. Org. Chem., 1973, 38, 1578; D. Baldwin and P. Van den Broek, J. Chem. Soc., Perkin Trans. 1, 1975, 375; R. K. Howe, T. A. Gruner, and J. E. Franz, J. Org. Chem., 1977, 42, 1813; J. Goerdeler and K. Nandi, Chem. Ber., 1981, 114, 549; S. Kabashima, T. Okawara, T. Yamasaki, and M. Furukawa, J. Heterocycl. Chem., 1991, 28, 1957.
5. 2O in a large scale: E. Muehlbauer and W. Weiss, German Pat. 1233882 (Chem. Abstr., 1967, 66, 95023j). As for applications of 1: K. Pilgram and R. D. Skiles, J. Org. Chem., 1973, 38, 1578; D. Baldwin and P. Van den Broek, J. Chem. Soc., Perkin Trans. 1, 1975, 375; R. K. Howe, T. A. Gruner, and J. E. Franz, J. Org. Chem., 1977, 42, 1813; J. Goerdeler and K. Nandi, Chem. Ber., 1981, 114, 549; S. Kabashima, T. Okawara, T. Yamasaki, and M. Furukawa, J. Heterocycl. Chem., 1991, 28, 1957.
6. 2O in a large scale: E. Muehlbauer and W. Weiss, German Pat. 1233882 (Chem. Abstr., 1967, 66, 95023j). As for applications of 1: K. Pilgram and R. D. Skiles, J. Org. Chem., 1973, 38, 1578; D. Baldwin and P. Van den Broek, J. Chem. Soc., Perkin Trans. 1, 1975, 375; R. K. Howe, T. A. Gruner, and J. E. Franz, J. Org. Chem., 1977, 42, 1813; J. Goerdeler and K. Nandi, Chem. Ber., 1981, 114, 549; S. Kabashima, T. Okawara, T. Yamasaki, and M. Furukawa, J. Heterocycl. Chem., 1991, 28, 1957.
7. 2O in a large scale: E. Muehlbauer and W. Weiss, German Pat. 1233882 (Chem. Abstr., 1967, 66, 95023j). As for applications of 1: K. Pilgram and R. D. Skiles, J. Org. Chem., 1973, 38, 1578; D. Baldwin and P. Van den Broek, J. Chem. Soc., Perkin Trans. 1, 1975, 375; R. K. Howe, T. A. Gruner, and J. E. Franz, J. Org. Chem., 1977, 42, 1813; J. Goerdeler and K. Nandi, Chem. Ber., 1981, 114, 549; S. Kabashima, T. Okawara, T. Yamasaki, and M. Furukawa, J. Heterocycl. Chem., 1991, 28, 1957.
8. 2O in a large scale: E. Muehlbauer and W. Weiss, German Pat. 1233882 (Chem. Abstr., 1967, 66, 95023j). As for applications of 1: K. Pilgram and R. D. Skiles, J. Org. Chem., 1973, 38, 1578; D. Baldwin and P. Van den Broek, J. Chem. Soc., Perkin Trans. 1, 1975, 375; R. K. Howe, T. A. Gruner, and J. E. Franz, J. Org. Chem., 1977, 42, 1813; J. Goerdeler and K. Nandi, Chem. Ber., 1981, 114, 549; S. Kabashima, T. Okawara, T. Yamasaki, and M. Furukawa, J. Heterocycl. Chem., 1991, 28, 1957.
9. 2O in a large scale: E. Muehlbauer and W. Weiss, German Pat. 1233882 (Chem. Abstr., 1967, 66, 95023j). As for applications of 1: K. Pilgram and R. D. Skiles, J. Org. Chem., 1973, 38, 1578; D. Baldwin and P. Van den Broek, J. Chem. Soc., Perkin Trans. 1, 1975, 375; R. K. Howe, T. A. Gruner, and J. E. Franz, J. Org. Chem., 1977, 42, 1813; J. Goerdeler and K. Nandi, Chem. Ber., 1981, 114, 549; S. Kabashima, T. Okawara, T. Yamasaki, and M. Furukawa, J. Heterocycl. Chem., 1991, 28, 1957.
10. For recent studies: Y. Tanabe, H. Yamamoto, M. Murakami, K. Yanagi, Y. Kubota, H. Okumura, Y. Sanemitsu, and G. Suzukamo, J. Chem. Soc., Perkin Trans. 1, 1995, 935; Y. Tanabe, H. Okumura, M. Nagaosa, and M. Murakami, Bull. Chem. Soc. Jpn., 1995, 68, 1467; Y. Tanabe, M. Nagaosa, and Y. Nishü, Heterocycles, 1995, 33, 2033.
11. For recent studies: Y. Tanabe, H. Yamamoto, M. Murakami, K. Yanagi, Y. Kubota, H. Okumura, Y. Sanemitsu, and G. Suzukamo, J. Chem. Soc., Perkin Trans. 1, 1995, 935; Y. Tanabe, H. Okumura, M. Nagaosa, and M. Murakami, Bull. Chem. Soc. Jpn., 1995, 68, 1467; Y. Tanabe, M. Nagaosa, and Y. Nishü, Heterocycles, 1995, 33, 2033.
12. For recent studies: Y. Tanabe, H. Yamamoto, M. Murakami, K. Yanagi, Y. Kubota, H. Okumura, Y. Sanemitsu, and G. Suzukamo, J. Chem. Soc., Perkin Trans. 1, 1995, 935; Y. Tanabe, H. Okumura, M. Nagaosa, and M. Murakami, Bull. Chem. Soc. Jpn., 1995, 68, 1467; Y. Tanabe, M. Nagaosa, and Y. Nishü, Heterocycles, 1995, 33, 2033.
13. Y. Tanabe, T. Okabe, A. Kakimizu, N. Ohno, and H. Yoshioka, Bull. Chem. Soc. Jpn., 1983, 56, 1255; Y. Tanabe and Y. Sanemitsu, Synthesis, 1988, 482.
14. Y. Tanabe, T. Okabe, A. Kakimizu, N. Ohno, and H. Yoshioka, Bull. Chem. Soc. Jpn., 1983, 56, 1255; Y. Tanabe and Y. Sanemitsu, Synthesis, 1988, 482.
15. Another practical methods for preparing 2(3H)-benzothiazolones were reported: (1) K. Konishi, I. Nishiguchi, and T. Hiroshima, Synthesis, 1984, 254; S. Umino, I. Ueda, and M. Masaaki, Japan Pat., 1973, 78167 (Chem. Abstr., 1974, 80, 82940v).
16. Another practical methods for preparing 2(3H)-benzothiazolones were reported: (1) K. Konishi, I. Nishiguchi, and T. Hiroshima, Synthesis, 1984, 254; S. Umino, I. Ueda, and M. Masaaki, Japan Pat., 1973, 78167 (Chem. Abstr., 1974, 80, 82940v).
17. a) J. B. Metzer, 'Comprehensive Heterocyclic Chemistry,' ed by A. Katritzky, Pergamon, Oxford, 1984, Vol. 6, p. 235.
18. b) T. Uematsu, S. Inoue, and N. Yamashita, Ger. Offen., 1978, 2801868, (Chem. Abstr., 1978, 89, 179989s).
19. I. Ueda, Japan Pat., 1979, 92956 (Chem. Abstr., 1980, 92, 94383b).
20. Y. Sanemitsu, S. Kawamura, and Y. Tanabe, J. Org. Chem., 1992, 57, 1053.
21. Y. Tanabe, T. Makita, and K. Mori, Chem. Lett., 1994, 2275.
22. For example; J. March, 'Advanced Organic Chemistry,' 3rd ed., Wiley, New York, 1985, p. 804.