Application of carbodiimide in heterocyclic synthesis: New facile synthesis of 2-aminoimidazolinone derivatives

Synthetic Communications

Volumn 27, Issue 20, 1997, Pages 3657-3662

  Ding, Ming Wu ^a   Tu, Hai Yang ^a   Liu, Zhao Jie ^a  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 4H IMIDAZOLINONE DERIVATIVE; CYANAMIDE; HETEROCYCLIC COMPOUND; IMIDAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030864561     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708007088     Document Type: Article

References (22)

1. Guella, G.; Mancini, I.; Zibrowius, H.; Pietra, F. Helv. Chim. Acta., 1989, 72, 1444; Djura, P.; Faulkner, D. J. J. Org. Chem., 1980, 45; 735; Debitus, C.; Cesario, M.; Guilhem, J.; Pascard, C.; Pais, M. Tetrahedron Lett., 1989, 30, 1535.
2. Guella, G.; Mancini, I.; Zibrowius, H.; Pietra, F. Helv. Chim. Acta., 1989, 72, 1444; Djura, P.; Faulkner, D. J. J. Org. Chem., 1980, 45; 735; Debitus, C.; Cesario, M.; Guilhem, J.; Pascard, C.; Pais, M. Tetrahedron Lett., 1989, 30, 1535.
3. Guella, G.; Mancini, I.; Zibrowius, H.; Pietra, F. Helv. Chim. Acta., 1989, 72, 1444; Djura, P.; Faulkner, D. J. J. Org. Chem., 1980, 45; 735; Debitus, C.; Cesario, M.; Guilhem, J.; Pascard, C.; Pais, M. Tetrahedron Lett., 1989, 30, 1535.
4. Lehr, H.; Karlan, S.; Goldberg, M. W., J. Am. Chem. Soc. 1953, 75, 3640; Cole, J. O.; Ronzio, A. R., J. Am. Chem. Soc., 1944, 66, 1584; Devasia, G. M.; Shafi, P. M., Indian J. Chem., 1979, 17B, 526; 1981, 20B, 657.; Kumar, P.; Makerjee, A. K., Indian J. Chem., 1979, 18B, 240.; Bonner, W.; Hermann, D., Ann. 1978, 1704.; Ashare, R.; Mukerjee, A. K., Indian J. Chem. Soc., Sect. B, 1986, 25B, 762.
5. Lehr, H.; Karlan, S.; Goldberg, M. W., J. Am. Chem. Soc. 1953, 75, 3640; Cole, J. O.; Ronzio, A. R., J. Am. Chem. Soc., 1944, 66, 1584; Devasia, G. M.; Shafi, P. M., Indian J. Chem., 1979, 17B, 526; 1981, 20B, 657.; Kumar, P.; Makerjee, A. K., Indian J. Chem., 1979, 18B, 240.; Bonner, W.; Hermann, D., Ann. 1978, 1704.; Ashare, R.; Mukerjee, A. K., Indian J. Chem. Soc., Sect. B, 1986, 25B, 762.
6. Lehr, H.; Karlan, S.; Goldberg, M. W., J. Am. Chem. Soc. 1953, 75, 3640; Cole, J. O.; Ronzio, A. R., J. Am. Chem. Soc., 1944, 66, 1584; Devasia, G. M.; Shafi, P. M., Indian J. Chem., 1979, 17B, 526; 1981, 20B, 657.; Kumar, P.; Makerjee, A. K., Indian J. Chem., 1979, 18B, 240.; Bonner, W.; Hermann, D., Ann. 1978, 1704.; Ashare, R.; Mukerjee, A. K., Indian J. Chem. Soc., Sect. B, 1986, 25B, 762.
7. Lehr, H.; Karlan, S.; Goldberg, M. W., J. Am. Chem. Soc. 1953, 75, 3640; Cole, J. O.; Ronzio, A. R., J. Am. Chem. Soc., 1944, 66, 1584; Devasia, G. M.; Shafi, P. M., Indian J. Chem., 1979, 17B, 526; 1981, 20B, 657.; Kumar, P.; Makerjee, A. K., Indian J. Chem., 1979, 18B, 240.; Bonner, W.; Hermann, D., Ann. 1978, 1704.; Ashare, R.; Mukerjee, A. K., Indian J. Chem. Soc., Sect. B, 1986, 25B, 762.
8. Lehr, H.; Karlan, S.; Goldberg, M. W., J. Am. Chem. Soc. 1953, 75, 3640; Cole, J. O.; Ronzio, A. R., J. Am. Chem. Soc., 1944, 66, 1584; Devasia, G. M.; Shafi, P. M., Indian J. Chem., 1979, 17B, 526; 1981, 20B, 657.; Kumar, P.; Makerjee, A. K., Indian J. Chem., 1979, 18B, 240.; Bonner, W.; Hermann, D., Ann. 1978, 1704.; Ashare, R.; Mukerjee, A. K., Indian J. Chem. Soc., Sect. B, 1986, 25B, 762.
9. Lehr, H.; Karlan, S.; Goldberg, M. W., J. Am. Chem. Soc. 1953, 75, 3640; Cole, J. O.; Ronzio, A. R., J. Am. Chem. Soc., 1944, 66, 1584; Devasia, G. M.; Shafi, P. M., Indian J. Chem., 1979, 17B, 526; 1981, 20B, 657.; Kumar, P.; Makerjee, A. K., Indian J. Chem., 1979, 18B, 240.; Bonner, W.; Hermann, D., Ann. 1978, 1704.; Ashare, R.; Mukerjee, A. K., Indian J. Chem. Soc., Sect. B, 1986, 25B, 762.
10. Lehr, H.; Karlan, S.; Goldberg, M. W., J. Am. Chem. Soc. 1953, 75, 3640; Cole, J. O.; Ronzio, A. R., J. Am. Chem. Soc., 1944, 66, 1584; Devasia, G. M.; Shafi, P. M., Indian J. Chem., 1979, 17B, 526; 1981, 20B, 657.; Kumar, P.; Makerjee, A. K., Indian J. Chem., 1979, 18B, 240.; Bonner, W.; Hermann, D., Ann. 1978, 1704.; Ashare, R.; Mukerjee, A. K., Indian J. Chem. Soc., Sect. B, 1986, 25B, 762.
11. Takeuchi, H.; Hagiwara, S.; Eguchi, S., Tetrahedron, 1989, 45, 6375.
12. Ding, M. W.; Shi, D. Q.; Xiao, W. J.; Huang, W. F.; Wu, T. J., Phosphorus, Sulfur and Silicon, 1995, 102, 59.; Chinese J. Applied Chem. 1995, 12, 9.; Chem. J. Chin. Univ. 1995, 16, 1396.
13. Ding, M. W.; Shi, D. Q.; Xiao, W. J.; Huang, W. F.; Wu, T. J., Phosphorus, Sulfur and Silicon, 1995, 102, 59.; Chinese J. Applied Chem. 1995, 12, 9.; Chem. J. Chin. Univ. 1995, 16, 1396.
14. Ding, M. W.; Shi, D. Q.; Xiao, W. J.; Huang, W. F.; Wu, T. J., Phosphorus, Sulfur and Silicon, 1995, 102, 59.; Chinese J. Applied Chem. 1995, 12, 9.; Chem. J. Chin. Univ. 1995, 16, 1396.
15. For recent examples of application of carbodiimide in heterocyclic synthesis, see: Okawa, T.; Eguchi, S.; Kakehi, A. J. Chem. Soc., Perkin. Trans. I, 1996, 247.; Wamhoff, H.; Bamberg, C.; Herrmann, S.; Nieger, M. J. Org. Chem., 1994, 59, 3985.; Molina, P.; Alajarin, M.; Vidal, A., Tetrahedron, 1995, 51, 5351.; Molina, P.; Alias, A.; Balado, A.; Arques, A., Liebigs Ann. Chem. 1994, 745.; Rodrigues, J. A. R.; Leiva, G. C; de Sousa, D. F., Tetrahedron Lett., 1995, 36, 59.; Molina, P.; Aller, E.; Ecija, M.; Lorenzo, A. Synthesis, 1996, 690; or see the review: Molina, P.; Vilaplana, M. J. Synthesis, 1994, 1197.
16. For recent examples of application of carbodiimide in heterocyclic synthesis, see: Okawa, T.; Eguchi, S.; Kakehi, A. J. Chem. Soc., Perkin. Trans. I, 1996, 247.; Wamhoff, H.; Bamberg, C.; Herrmann, S.; Nieger, M. J. Org. Chem., 1994, 59, 3985.; Molina, P.; Alajarin, M.; Vidal, A., Tetrahedron, 1995, 51, 5351.; Molina, P.; Alias, A.; Balado, A.; Arques, A., Liebigs Ann. Chem. 1994, 745.; Rodrigues, J. A. R.; Leiva, G. C; de Sousa, D. F., Tetrahedron Lett., 1995, 36, 59.; Molina, P.; Aller, E.; Ecija, M.; Lorenzo, A. Synthesis, 1996, 690; or see the review: Molina, P.; Vilaplana, M. J. Synthesis, 1994, 1197.
17. For recent examples of application of carbodiimide in heterocyclic synthesis, see: Okawa, T.; Eguchi, S.; Kakehi, A. J. Chem. Soc., Perkin. Trans. I, 1996, 247.; Wamhoff, H.; Bamberg, C.; Herrmann, S.; Nieger, M. J. Org. Chem., 1994, 59, 3985.; Molina, P.; Alajarin, M.; Vidal, A., Tetrahedron, 1995, 51, 5351.; Molina, P.; Alias, A.; Balado, A.; Arques, A., Liebigs Ann. Chem. 1994, 745.; Rodrigues, J. A. R.; Leiva, G. C; de Sousa, D. F., Tetrahedron Lett., 1995, 36, 59.; Molina, P.; Aller, E.; Ecija, M.; Lorenzo, A. Synthesis, 1996, 690; or see the review: Molina, P.; Vilaplana, M. J. Synthesis, 1994, 1197.
18. For recent examples of application of carbodiimide in heterocyclic synthesis, see: Okawa, T.; Eguchi, S.; Kakehi, A. J. Chem. Soc., Perkin. Trans. I, 1996, 247.; Wamhoff, H.; Bamberg, C.; Herrmann, S.; Nieger, M. J. Org. Chem., 1994, 59, 3985.; Molina, P.; Alajarin, M.; Vidal, A., Tetrahedron, 1995, 51, 5351.; Molina, P.; Alias, A.; Balado, A.; Arques, A., Liebigs Ann. Chem. 1994, 745.; Rodrigues, J. A. R.; Leiva, G. C; de Sousa, D. F., Tetrahedron Lett., 1995, 36, 59.; Molina, P.; Aller, E.; Ecija, M.; Lorenzo, A. Synthesis, 1996, 690; or see the review: Molina, P.; Vilaplana, M. J. Synthesis, 1994, 1197.
19. For recent examples of application of carbodiimide in heterocyclic synthesis, see: Okawa, T.; Eguchi, S.; Kakehi, A. J. Chem. Soc., Perkin. Trans. I, 1996, 247.; Wamhoff, H.; Bamberg, C.; Herrmann, S.; Nieger, M. J. Org. Chem., 1994, 59, 3985.; Molina, P.; Alajarin, M.; Vidal, A., Tetrahedron, 1995, 51, 5351.; Molina, P.; Alias, A.; Balado, A.; Arques, A., Liebigs Ann. Chem. 1994, 745.; Rodrigues, J. A. R.; Leiva, G. C; de Sousa, D. F., Tetrahedron Lett., 1995, 36, 59.; Molina, P.; Aller, E.; Ecija, M.; Lorenzo, A. Synthesis, 1996, 690; or see the review: Molina, P.; Vilaplana, M. J. Synthesis, 1994, 1197.
20. For recent examples of application of carbodiimide in heterocyclic synthesis, see: Okawa, T.; Eguchi, S.; Kakehi, A. J. Chem. Soc., Perkin. Trans. I, 1996, 247.; Wamhoff, H.; Bamberg, C.; Herrmann, S.; Nieger, M. J. Org. Chem., 1994, 59, 3985.; Molina, P.; Alajarin, M.; Vidal, A., Tetrahedron, 1995, 51, 5351.; Molina, P.; Alias, A.; Balado, A.; Arques, A., Liebigs Ann. Chem. 1994, 745.; Rodrigues, J. A. R.; Leiva, G. C; de Sousa, D. F., Tetrahedron Lett., 1995, 36, 59.; Molina, P.; Aller, E.; Ecija, M.; Lorenzo, A. Synthesis, 1996, 690; or see the review: Molina, P.; Vilaplana, M. J. Synthesis, 1994, 1197.
21. For recent examples of application of carbodiimide in heterocyclic synthesis, see: Okawa, T.; Eguchi, S.; Kakehi, A. J. Chem. Soc., Perkin. Trans. I, 1996, 247.; Wamhoff, H.; Bamberg, C.; Herrmann, S.; Nieger, M. J. Org. Chem., 1994, 59, 3985.; Molina, P.; Alajarin, M.; Vidal, A., Tetrahedron, 1995, 51, 5351.; Molina, P.; Alias, A.; Balado, A.; Arques, A., Liebigs Ann. Chem. 1994, 745.; Rodrigues, J. A. R.; Leiva, G. C; de Sousa, D. F., Tetrahedron Lett., 1995, 36, 59.; Molina, P.; Aller, E.; Ecija, M.; Lorenzo, A. Synthesis, 1996, 690; or see the review: Molina, P.; Vilaplana, M. J. Synthesis, 1994, 1197.
22. Molina, P.; Alajarin, M.; Lopez-Leonardo, C., J. prakt. Chem. 1993, 335, 305.