Preparation of bicyclic guanidines by the iodocyclization of 3-alkenyl-2-(substituted amino)-1-imidazolin-4-ones

Heterocyclic Communications

Volumn 2, Issue 4, 1996, Pages 361-370

  Noguchi, Michihiko ^a   Okada, Hiroshi ^a   Watanabe, Masanori ^a   Moriyama, Hideki ^a   Nakamura, Osamu ^a   Kakehi, Akikazu ^b  

^a YAMAGUCHI UNIVERSITY   (Japan)

^b SHINSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010725497     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (20)

1. (a) Preparation of Heterocycles Using Functionalized Heterocumulenes. Part 6.
2. (b) Part 5. in this series: Noguchi, M.; Okada, H.; Watanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581.
3. Watanabe, M.; Okada, R; Teshima, T.; Noguchi, M.; Kakehi, A. Tetrahedron 1996, 52, 2827.
4. Kosasayama, A.; Konno, T.; Higashi, K.; Ishikawa, F. Chem. Pharm. Bull. 1979, 27, 841. Also see references cited therein.
5. For recent reviews on the synthetic utilities of carbodiimides: Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197; Eguchi, S.; Matsushita, Y.; Yamashita, K. Org. Prep. Proced. Int. 1992, 24, 209; Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353.
6. For recent reviews on the synthetic utilities of carbodiimides: Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197; Eguchi, S.; Matsushita, Y.; Yamashita, K. Org. Prep. Proced. Int. 1992, 24, 209; Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353.
7. For recent reviews on the synthetic utilities of carbodiimides: Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197; Eguchi, S.; Matsushita, Y.; Yamashita, K. Org. Prep. Proced. Int. 1992, 24, 209; Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353.
8. For recent reviews on the iodocyclizations: Boivin, T. L. B. Tetrahedron 1987, 43, 3309; Cardillo, G.; Orena, M. Ibid. 1990, 46, 3321.
9. For recent reviews on the iodocyclizations: Boivin, T. L. B. Tetrahedron 1987, 43, 3309; Cardillo, G.; Orena, M. Ibid. 1990, 46, 3321.
10. The authors have deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained on request from the Director, Cambridge Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge CB21EW, U.K.
11. The reversibility of the three-membered halonium ion formation (containing iodonium ion) has been detailed. As recent papers: Reitz, A. B.; Nortey, S. O.; Maryanoff, B. E.; Liotta, D.; Momahan, R. III. J. Org. Chem. 1987, 52, 4191; Labell, M.; Guindon, Y. J. Am. Chem. Soc. 1989, 111, 2204; Brown, R. S.; Slebocka-Tilk, H.; Bennet, A. J.; Bellucci, G.; Bianchini, R.; Ambrosetti, R. Ibid. 1990, 112, 6310; Brown, R. S.; Nagorski, R. W.; Bennet, A. J.; McClung, R. E. D.; Aarts, G. H. M.; Klobukowski, M.; McDonald, R.; Santarsiero, B. D. Ibid. 1994, 116, 2448. Also see the references cited therein.
12. The reversibility of the three-membered halonium ion formation (containing iodonium ion) has been detailed. As recent papers: Reitz, A. B.; Nortey, S. O.; Maryanoff, B. E.; Liotta, D.; Momahan, R. III. J. Org. Chem. 1987, 52, 4191; Labell, M.; Guindon, Y. J. Am. Chem. Soc. 1989, 111, 2204; Brown, R. S.; Slebocka-Tilk, H.; Bennet, A. J.; Bellucci, G.; Bianchini, R.; Ambrosetti, R. Ibid. 1990, 112, 6310; Brown, R. S.; Nagorski, R. W.; Bennet, A. J.; McClung, R. E. D.; Aarts, G. H. M.; Klobukowski, M.; McDonald, R.; Santarsiero, B. D. Ibid. 1994, 116, 2448. Also see the references cited therein.
13. The reversibility of the three-membered halonium ion formation (containing iodonium ion) has been detailed. As recent papers: Reitz, A. B.; Nortey, S. O.; Maryanoff, B. E.; Liotta, D.; Momahan, R. III. J. Org. Chem. 1987, 52, 4191; Labell, M.; Guindon, Y. J. Am. Chem. Soc. 1989, 111, 2204; Brown, R. S.; Slebocka-Tilk, H.; Bennet, A. J.; Bellucci, G.; Bianchini, R.; Ambrosetti, R. Ibid. 1990, 112, 6310; Brown, R. S.; Nagorski, R. W.; Bennet, A. J.; McClung, R. E. D.; Aarts, G. H. M.; Klobukowski, M.; McDonald, R.; Santarsiero, B. D. Ibid. 1994, 116, 2448. Also see the references cited therein.
14. The reversibility of the three-membered halonium ion formation (containing iodonium ion) has been detailed. As recent papers: Reitz, A. B.; Nortey, S. O.; Maryanoff, B. E.; Liotta, D.; Momahan, R. III. J. Org. Chem. 1987, 52, 4191; Labell, M.; Guindon, Y. J. Am. Chem.Soc. 1989, 111, 2204; Brown, R. S.; Slebocka-Tilk, H.; Bennet, A. J.; Bellucci, G.; Bianchini, R.; Ambrosetti, R. Ibid. 1990, 112, 6310; Brown, R. S.; Nagorski, R. W.; Bennet, A. J.; McClung, R. E. D.; Aarts, G. H. M.; Klobukowski, M.; McDonald, R.; Santarsiero, B. D. Ibid. 1994, 116, 2448. Also see the references cited therein.
15. Koziara, A.; Osowska-Pacewicka, K.; Zawadzki, S.; Zwierzak, A. Synthesis 1985, 202.
16. Roberts, J. D.; Mazur, R. H. J. Am. Chem. Soc. 1951, 73, 2509; Semenow, D. C.-H. Shin, Young, W. G. Ibid. 1958, 80, 5472.
17. Roberts, J. D.; Mazur, R. H. J. Am. Chem. Soc. 1951, 73, 2509; Semenow, D. C.-H. Shin, Young, W. G. Ibid. 1958, 80, 5472.
18. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrikson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 221.
19. Stewart, J. J.J. Comput. Chem. 1989, 10, 209.
20. "MOPAC program version 6, QCPE No. 455," 1990, Department of Chemistry, Indiana University, Bloomington, IN 47405.