Synthesis of 2-Monosubstituted Pyrroles by Intramolecular Addition of Amines via Reductive Amination with Dibutyliodotin Hydride Complex (Bu 2SnIH-HMPA)

Synlett

Volumn , Issue 1, 2004, Pages 137-139

  Shibata, Ikuya ^a   Kato, Hirofumi ^a   Kanazawa, Nobuaki ^a   Yasuda, Makoto ^a   Baba, Akio ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Complex; Pyrroles; Reductive amination; Tin hydride

Indexed keywords

AMINE; PYRROLE DERIVATIVE;

AMINOHYDROXYLATION; ARTICLE; REDUCTION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0346340897     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-43371     Document Type: Article

References (22)

1. Shibata, I.; Moriuchi-Kawakami, T.; Tanizawa, D.; Suwa, T.; Sugiyama, E. ; Matsuda, H.; Baba, A. J. Org. Chem. 1998, 63, 383.
2. Suwa, T.; Sugiyama, E.; Shibata, I.; Baba, A. Synlett 2000, 556.
3. For most recent work, see: Lee, C.-F.; Yang, L.-M.; Hwu, T.-Y.; Feng, A.-S.; Tseng, J.-C.; Luh, T.-Y. J. Am. Chem. Soc. 2000, 122, 4992; and references therein.
4. For a review see: (a) Gossauer, A. In Pyrrole, Houben-Weyl, Methods in Organic Chemistry, Vol. E6a/1; Thieme: Stuttgart, 1994, 556. (b) See also: Boger, D. L.; Boyce, C. W.; Labroli, M. A.; Sehon, C. A.; Jin, Q. J. Am. Chem. Soc. 1999, 121, 54. (c) Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1998, 120, 2817. (d) See further: Sayah, B.; Pelloux-Leon, N.; Vallee, Y. J. Org. Chem. 2000, 65, 2824. (e) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587.
5. For a review see: (a) Gossauer, A. In Pyrrole, Houben-Weyl, Methods in Organic Chemistry, Vol. E6a/1; Thieme: Stuttgart, 1994, 556. (b) See also: Boger, D. L.; Boyce, C. W.; Labroli, M. A.; Sehon, C. A.; Jin, Q. J. Am. Chem. Soc. 1999, 121, 54. (c) Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1998, 120, 2817. (d) See further: Sayah, B.; Pelloux-Leon, N.; Vallee, Y. J. Org. Chem. 2000, 65, 2824. (e) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587.
6. For a review see: (a) Gossauer, A. In Pyrrole, Houben-Weyl, Methods in Organic Chemistry, Vol. E6a/1; Thieme: Stuttgart, 1994, 556. (b) See also: Boger, D. L.; Boyce, C. W.; Labroli, M. A.; Sehon, C. A.; Jin, Q. J. Am. Chem. Soc. 1999, 121, 54. (c) Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1998, 120, 2817. (d) See further: Sayah, B.; Pelloux-Leon, N.; Vallee, Y. J. Org. Chem. 2000, 65, 2824. (e) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587.
7. For a review see: (a) Gossauer, A. In Pyrrole, Houben-Weyl, Methods in Organic Chemistry, Vol. E6a/1; Thieme: Stuttgart, 1994, 556. (b) See also: Boger, D. L.; Boyce, C. W.; Labroli, M. A.; Sehon, C. A.; Jin, Q. J. Am. Chem. Soc. 1999, 121, 54. (c) Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1998, 120, 2817. (d) See further: Sayah, B.; Pelloux-Leon, N.; Vallee, Y. J. Org. Chem. 2000, 65, 2824. (e) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587.
8. For a review see: (a) Gossauer, A. In Pyrrole, Houben-Weyl, Methods in Organic Chemistry, Vol. E6a/1; Thieme: Stuttgart, 1994, 556. (b) See also: Boger, D. L.; Boyce, C. W.; Labroli, M. A.; Sehon, C. A.; Jin, Q. J. Am. Chem. Soc. 1999, 121, 54. (c) Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1998, 120, 2817. (d) See further: Sayah, B.; Pelloux-Leon, N.; Vallee, Y. J. Org. Chem. 2000, 65, 2824. (e) Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587.
9. 4a (b) See also: Gadzhily, R. A.; Fedoseev, V. M.; Dzhafarov, V. G. Chem. Heterocycl. Compd. 1990, 26, 874. (c) Engel, N.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 676. (d) For syntheses of 2-monosubstituted pyrroles via acylation-reduction or alkylation of pyrrole see, for example: Garrido, D. O. A.; Buldain, G.; Frydman, B. J. Org. Chem. 1984, 49, 2619. (e) Muchowski, J. M. ; Solas, D. R. J. Org. Chem. 1984, 49, 203. (f) See also: Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074.
10. 4a (b) See also: Gadzhily, R. A.; Fedoseev, V. M.; Dzhafarov, V. G. Chem. Heterocycl. Compd. 1990, 26, 874. (c) Engel, N.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 676. (d) For syntheses of 2-monosubstituted pyrroles via acylation-reduction or alkylation of pyrrole see, for example: Garrido, D. O. A.; Buldain, G.; Frydman, B. J. Org. Chem. 1984, 49, 2619. (e) Muchowski, J. M. ; Solas, D. R. J. Org. Chem. 1984, 49, 203. (f) See also: Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074.
11. 4a (b) See also: Gadzhily, R. A.; Fedoseev, V. M.; Dzhafarov, V. G. Chem. Heterocycl. Compd. 1990, 26, 874. (c) Engel, N.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 676. (d) For syntheses of 2-monosubstituted pyrroles via acylation-reduction or alkylation of pyrrole see, for example: Garrido, D. O. A.; Buldain, G.; Frydman, B. J. Org. Chem. 1984, 49, 2619. (e) Muchowski, J. M. ; Solas, D. R. J. Org. Chem. 1984, 49, 203. (f) See also: Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074.
12. 4a (b) See also: Gadzhily, R. A.; Fedoseev, V. M.; Dzhafarov, V. G. Chem. Heterocycl. Compd. 1990, 26, 874. (c) Engel, N.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 676. (d) For syntheses of 2-monosubstituted pyrroles via acylation-reduction or alkylation of pyrrole see, for example: Garrido, D. O. A.; Buldain, G.; Frydman, B. J. Org. Chem. 1984, 49, 2619. (e) Muchowski, J. M. ; Solas, D. R. J. Org. Chem. 1984, 49, 203. (f) See also: Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074.
13. 4a (b) See also: Gadzhily, R. A.; Fedoseev, V. M.; Dzhafarov, V. G. Chem. Heterocycl. Compd. 1990, 26, 874. (c) Engel, N.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 676. (d) For syntheses of 2-monosubstituted pyrroles via acylation-reduction or alkylation of pyrrole see, for example: Garrido, D. O. A.; Buldain, G.; Frydman, B. J. Org. Chem. 1984, 49, 2619. (e) Muchowski, J. M. ; Solas, D. R. J. Org. Chem. 1984, 49, 203. (f) See also: Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074.
14. 4a (b) See also: Gadzhily, R. A.; Fedoseev, V. M.; Dzhafarov, V. G. Chem. Heterocycl. Compd. 1990, 26, 874. (c) Engel, N.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 676. (d) For syntheses of 2-monosubstituted pyrroles via acylation-reduction or alkylation of pyrrole see, for example: Garrido, D. O. A.; Buldain, G.; Frydman, B. J. Org. Chem. 1984, 49, 2619. (e) Muchowski, J. M. ; Solas, D. R. J. Org. Chem. 1984, 49, 203. (f) See also: Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074.
15. For preparation of 1, see: Kobayashi, Y.; Nakano, M.; Kumar, G. B.; Kishihara, K. J. Org. Chem. 1998, 63, 7505.
16. 12NCl: 253.0658. Found: 253.0653.
17. Kawakami, T.; Shibata, I.; Baba, A. J. Org. Chem. 1996, 61, 82.
18. We have already reported the increase of nucleophilicity of Sn-N bonds by pentacoordination, see: (a) Shibata, I.; Baba, A.; Iwasaki, H.; Matsuda, H. J. Org. Chem. 1986, 51, 2177. (b) Baba, A.; Kishiki, H.; Shibata, I.; Matsuda, H. Organometallics 1984, 4, 1329. (c) Shibata, I.; Baba, A.; Matsuda, H. J. Chem. Soc., Chem. Commun. 1986, 1703. (d) Shibata, I.; Nakamura, K.; Baba, A.; Matsuda, H. Bull. Chem. Soc. Jpn. 1989, 62, 853.
19. We have already reported the increase of nucleophilicity of Sn-N bonds by pentacoordination, see: (a) Shibata, I.; Baba, A.; Iwasaki, H.; Matsuda, H. J. Org. Chem. 1986, 51, 2177. (b) Baba, A.; Kishiki, H.; Shibata, I.; Matsuda, H. Organometallics 1984, 4, 1329. (c) Shibata, I.; Baba, A.; Matsuda, H. J. Chem. Soc., Chem. Commun. 1986, 1703. (d) Shibata, I.; Nakamura, K.; Baba, A.; Matsuda, H. Bull. Chem. Soc. Jpn. 1989, 62, 853.
20. We have already reported the increase of nucleophilicity of Sn-N bonds by pentacoordination, see: (a) Shibata, I.; Baba, A.; Iwasaki, H.; Matsuda, H. J. Org. Chem. 1986, 51, 2177. (b) Baba, A.; Kishiki, H.; Shibata, I.; Matsuda, H. Organometallics 1984, 4, 1329. (c) Shibata, I.; Baba, A.; Matsuda, H. J. Chem. Soc., Chem. Commun. 1986, 1703. (d) Shibata, I.; Nakamura, K.; Baba, A.; Matsuda, H. Bull. Chem. Soc. Jpn. 1989, 62, 853.
21. We have already reported the increase of nucleophilicity of Sn-N bonds by pentacoordination, see: (a) Shibata, I.; Baba, A.; Iwasaki, H.; Matsuda, H. J. Org. Chem. 1986, 51, 2177. (b) Baba, A.; Kishiki, H.; Shibata, I.; Matsuda, H. Organometallics 1984, 4, 1329. (c) Shibata, I.; Baba, A.; Matsuda, H. J. Chem. Soc., Chem. Commun. 1986, 1703. (d) Shibata, I.; Nakamura, K.; Baba, A.; Matsuda, H. Bull. Chem. Soc. Jpn. 1989, 62, 853.
22. 2ClSnN-) does not has enough nucleophilicity to cause cyclization because of the electron withdrawing character of Cl-substituent (entry 4).