2-Chloro-1,3-dimethylimidazolinium chloride. 2. Its application to the construction of heterocycles through dehydration reactions

Journal of Organic Chemistry

Volumn 64, Issue 19, 1999, Pages 6989-6992

  Isobe, Toshio ^a   Ishikawa, Tsutomu ^b  

^a Shiratori Pharmaceutical Co Ltd   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 CHLORO 1,3 DIMETHYLIMIDAZOLINIUM CHLORIDE; DESICCANT; HETEROCYCLIC COMPOUND; IMIDAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; DESICCATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0033578789     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9909756     Document Type: Article

References (51)

1. Isobe, T.; Ishikawa, T. J. Org. Chem. 1999, 64, 6984.
2. Clapp, L. B. In Comprephensive Heterocyclic Chemistry; Katritzky, A., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984, Vol. 6, pp 376-378.
3. 6). It was obtained as nonhygroscopic colorless prisms, mp 231 °C dec [see Okamura, H.; Kawamoto, H.; Shiraishi, H. Eur. Patent EP 162308, 1985; Chem. Abstr. 1986, 104, 159540. Kiso, Y.; Fujiwara, Y.; Kimura, T.; Nishitani, A.; Akaji, K. Int. J. Peptide Protein Res. 1992, 40, 308]. CIP is now commercially available from Fluka (Y17500/5 g in Japan: this corresponds to $145.8/5 g, based on the exchange rate of ¥120/$ of Japanese yen to U.S. dollars). Other DMC analogues were similarly synthesized from the corresponding reactants and/or reagents according to the preparation method of 1 (see the Supporting Information).
4. 6). It was obtained as nonhygroscopic colorless prisms, mp 231 °C dec [see Okamura, H.; Kawamoto, H.; Shiraishi, H. Eur. Patent EP 162308, 1985; Chem. Abstr. 1986, 104, 159540. Kiso, Y.; Fujiwara, Y.; Kimura, T.; Nishitani, A.; Akaji, K. Int. J. Peptide Protein Res. 1992, 40, 308]. CIP is now commercially available from Fluka (Y17500/5 g in Japan: this corresponds to $145.8/5 g, based on the exchange rate of ¥120/$ of Japanese yen to U.S. dollars). Other DMC analogues were similarly synthesized from the corresponding reactants and/or reagents according to the preparation method of 1 (see the Supporting Information).
5. 6). It was obtained as nonhygroscopic colorless prisms, mp 231 °C dec [see Okamura, H.; Kawamoto, H.; Shiraishi, H. Eur. Patent EP 162308, 1985; Chem. Abstr. 1986, 104, 159540. Kiso, Y.; Fujiwara, Y.; Kimura, T.; Nishitani, A.; Akaji, K. Int. J. Peptide Protein Res. 1992, 40, 308]. CIP is now commercially available from Fluka (Y17500/5 g in Japan: this corresponds to $145.8/5 g, based on the exchange rate of ¥120/$ of Japanese yen to U.S. dollars). Other DMC analogues were similarly synthesized from the corresponding reactants and/or reagents according to the preparation method of 1 (see the Supporting Information).
6. Reference to the product in Table 1 is as follows. Thoman, C. J.; Voaden, D. J. Organic Syntheses; Wiley: New York, 1973; Collect. Vol. V, p 962.
7. Davies, D. E.; Storr, R. C. In Comprephensive Heterocyclic Chemistry; Katritzky, A., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 7, pp 247-267.
8. References to the products in Table 2 are as follows, (a) Runs 1, 3, and 5: Georg, G. I.; Mashava, P. M.; Guan, X. Tetrahedron Lett. 1991, 32, 581.
9. (b) Run 2: Isobe, T. Jpn. Kokai Tokkyo Koho JP 07 330721, 1995; Chem. Abstr. 1996, 124, 289241.
10. (b) Run 2: Isobe, T. Jpn. Kokai Tokkyo Koho JP 07 330721, 1995; Chem. Abstr. 1996, 124, 289241.
11. Run 4: Arrieta, A.; Aizpurua, J. M.; Palomo, C. Tetrahedron Lett. 1984, 25, 3365.
12. Georg, G. I.; Mashava, P. M.; Guan, X. Tetrahedron Lett. 1991, 32, 581.
13. Donnelly, D. M.; Storr, R. C. In Comprephensive Heterocyclic Chemistry, Katritzky, A., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 4, pp 658-684.
14. References to the products in Table 3 are as follows. (a) Run 1: Sakurai, K.; Matsumoto, H.; Adachi, J. Yakugaku Zasshi 1968, 88, 919; Chem. Abstr. 1968, 69, 94792.
15. References to the products in Table 3 are as follows. (a) Run 1: Sakurai, K.; Matsumoto, H.; Adachi, J. Yakugaku Zasshi 1968, 88, 919; Chem. Abstr. 1968, 69, 94792.
16. (b) Run 2: Isobe, T. Jpn, Kokai Tokkyo Koho JP 08 134054, 1996; Chem. Abstr. 1996, 125, 142531.
17. (b) Run 2: Isobe, T. Jpn, Kokai Tokkyo Koho JP 08 134054, 1996; Chem. Abstr. 1996, 125, 142531.
18. Run 3: Chan, C. C.; Farmer, P. S. Pharmazie 1986, 41, 835.
19. References to the products in Table 4 are as follows. (a) Run 1: Sauers, C. K. J. Org. Chem. 1969, 34, 2275.
20. (b) Run 2: Takase, I.; Matsuyama, T.; Kawamura, T. Kobunshi Ronbunshu 1982, 49, 513; Chem. Abstr. 1992, 117, 70395.
21. (b) Run 2: Takase, I.; Matsuyama, T.; Kawamura, T. Kobunshi Ronbunshu 1982, 49, 513; Chem. Abstr. 1992, 117, 70395.
22. Run 3: Capraro, H. G.; Rihs, G.; Martin, P. Helv. Chim. Acta 1983, 66, 633.
23. Boyd, G. V. In Comprephensive Heterocyclic Chemistry; Katritzky, A., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 6, pp 229-232.
24. References to the products in Table 5 are as follows. (a) Run 1: Marquez, A.; Chuaqui, C. A.; Rodriguez, H.; Zagal, L. Tetrahedron 1985, 41, 2341.
25. (b) Runs 2-4: Isobe, T.; Hosogai, A. Jpn. Kokai Tokkyo Koho JP 08 027132, 1996; Chem. Abstr. 1996, 124, 343280.
26. (b) Runs 2-4: Isobe, T.; Hosogai, A. Jpn. Kokai Tokkyo Koho JP 08 027132, 1996; Chem. Abstr. 1996, 124, 343280.
27. Reference to the products in runs 1 and 2 in Table 6 is as follows. Isobe, T.; Hosogai, A. Jpn. Kokai Tokkyo Koho JP 08 027132, 1996; Chem. Abstr. 1998, 124, 343280.
28. Reference to the products in runs 1 and 2 in Table 6 is as follows. Isobe, T.; Hosogai, A. Jpn. Kokai Tokkyo Koho JP 08 027132, 1996; Chem. Abstr. 1998, 124, 343280.
29. Glaser, R.; Geresh, S. Tetrahedron 1979, 35, 2381.
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31. (b) Runs 2 and 3: Isobe, T.; Fukuda, K.; Takashi, M. Jpn. Kokai Tokkyo Koho JP 09 124621, 1997; Chem. Abstr. 1997, 127, 50634.
32. (b) Runs 2 and 3: Isobe, T.; Fukuda, K.; Takashi, M. Jpn. Kokai Tokkyo Koho JP 09 124621, 1997; Chem. Abstr. 1997, 127, 50634.
33. Hill, J. In Comprephensive Heterocyclic Chemistry; Katritzky, A., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 6, pp 440-445.
34. References to the products in Table 8 are as follows. (a) Run 2: Siegrist, A. E. Helv. Chim. Acta 1967, 50, 906.
35. (b) Run 3: Hayes, F. N.; Rogers, B. S.; Ott, D. G. J. Am. Chem. Soc. 1955, 77, 1850.
36. References to the products in Table 9 are as follows. (a) Run 1: Sain, B.; Sandhu, J. S. Indian J. Chem. 1992, 31B, 768.
37. (b) Run 2: ref 17b.
38. Run 3: Rigo, B.; Cauliez, P.; Fasseur, D.; Couturier, D. Synth. Commun. 1986, 16, 1665.
39. References to the products in Table 10 are as follows. (a) Run 2: Hashimoto, N.; Deguchi, H.; Kojima, T.; Miyazaki, H. Jpn. Kokai Tokkyo Koho JP 03 163435, 1991; Chem. Abstr. 1992, 116, 162398.
40. References to the products in Table 10 are as follows. (a) Run 2: Hashimoto, N.; Deguchi, H.; Kojima, T.; Miyazaki, H. Jpn. Kokai Tokkyo Koho JP 03 163435, 1991; Chem. Abstr. 1992, 116, 162398.
41. (b) Runs 3-5: Isobe, T. Jpn. Kokai Tokkyo Koho JP 07 258234, 1995; Chem. Abstr. 1996, 124, 176109.
42. (b) Runs 3-5: Isobe, T. Jpn. Kokai Tokkyo Koho JP 07 258234, 1995; Chem. Abstr. 1996, 124, 176109.
43. Franz, J. E.; Dhingra, O. P. In Comprephensive Heterocyclic Chemistry; Katritzky, A., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 6, pp 492-501.
44. References to the products in Table 11 are as follows. (a) Run 1: Howe, R. K.; Franz, J. E. J. Org. Chem. 1974, 39, 962.
45. (b) Run 2: Podolesov, B. D.; Jordanovaka, V. B. J. Serb. Chem. Soc. 1985, 50, 119; Chem. Abstr. 1987, 106, 4944).
46. (b) Run 2: Podolesov, B. D.; Jordanovaka, V. B. J. Serb. Chem. Soc. 1985, 50, 119; Chem. Abstr. 1987, 106, 4944).
47. Sainsbury, M. In Comprephensive Heterocyclic Chemistry; Katritzky, A., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 3, pp 1018-1031.
48. References to the products in Table 12 are as follows. (a) Run 1: Reid, W.; Valentin, J. Chem. Ber. 1968, 101, 2106.
49. (b) Run 2: Bain, D. I.; Smalley, R. K. J. Chem. Soc. C 1968, 1593.
50. Run 3: Kojima, M.; Tsutsumi, N.; Ujiie, A.; Naito, J. Oyo Yakuri 1984, 28, 623; Chem. Abstr. 1985, 102, 55825.
51. Run 3: Kojima, M.; Tsutsumi, N.; Ujiie, A.; Naito, J. Oyo Yakuri 1984, 28, 623; Chem. Abstr. 1985, 102, 55825.