Nucleophilic substitution reactions of 1-methoxy-6-nitroindole-3-carbaldehyde 1

Heterocycles

Volumn 58, Issue , 2002, Pages 53-56

  Yamada, Koji ^a   Yamada, Fumio ^a   Shiraishi, Takei ^a   Tomioka, Saori ^a   Somei, Masanori ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 METHOXY 6 NITROINDOLE 3 CARBALDEHYDE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; ELECTRON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 0037159709     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-02-s(m)14     Document Type: Article

References (28)

1. a) Dedicated to the 70th birthday of Prof. A. I. Meyers.
2. b) This is Part 113 of a series entitled "The Chemistry of Indoles ".
3. c) Part 112: T. Hayashi, W. Peng, Y. Nakai, K. Yamada, and M. Somei, Heterocycles, 2002, 57, 421. All new compounds gave satisfactory spectral and elemental analysis or high-resolution MS spectral data for crystals or oil, respectively. 3e, mp 180-182 °C; 7, mp >300 °C; 8, mp >300 °C; 9, mp 300 °C; 10, mp >300 °C; 11, mp >300 °C; 12, mp 291-293 >C; 13, mp 268 -272 °C; 14, mp >300 °C; 15, mp 125-136 °C (decomp); 17, mp 242-244 °C; 18, mp 240-241 °C (decomp); 19, mp 217-219 °C (decomp).
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12. M. Somei, H. Morikawa, K. Yamada, and F. Yamada, Heterocycles, 1998, 48, 1117; J. A. Joule, "Progress in Heterocyclic Chemistry", Vol. 11, ed. by G. W. Gribble and T. L. Gilchrist, Elsevier Science Ltd., Oxford, 1999, pp. 45-65; M. Hasegawa, K. Yamada, Y. Nagahama, and M. Somei, Heterocycles, 1999, 51, 2815. See also references, 4 and 5.
13. M. Somei, H. Morikawa, K. Yamada, and F. Yamada, Heterocycles, 1998, 48, 1117; J. A. Joule, "Progress in Heterocyclic Chemistry", Vol. 11, ed. by G. W. Gribble and T. L. Gilchrist, Elsevier Science Ltd., Oxford, 1999, pp. 45-65; M. Hasegawa, K. Yamada, Y. Nagahama, and M. Somei, Heterocycles, 1999, 51, 2815. See also references, 4 and 5.
14. Review; M. Somei, J. Synth. Org. Chem. Jpn., 1991, 49, 205; M. Somei, T. Kawasaki, Y. Fukui, F. Yamada, T. Kobayashi, H. Aoyama, and D. Shinmyo, Heterocycles, 1992, 34, 1877; M. Somei and Y. Fukui, ibid., 1993, 36, 1859; M. Hasegawa, M. Tabata, K. Satoh, F. Yamada, and M. Somei, ibid., 1996, 43, 2333; Review: M. Somei, ibid., 1999, 50, 1157. See also reference 6b.
15. Review; M. Somei, J. Synth. Org. Chem. Jpn., 1991, 49, 205; M. Somei, T. Kawasaki, Y. Fukui, F. Yamada, T. Kobayashi, H. Aoyama, and D. Shinmyo, Heterocycles, 1992, 34, 1877; M. Somei and Y. Fukui, ibid., 1993, 36, 1859; M. Hasegawa, M. Tabata, K. Satoh, F. Yamada, and M. Somei, ibid., 1996, 43, 2333; Review: M. Somei, ibid., 1999, 50, 1157. See also reference 6b.
16. Review; M. Somei, J. Synth. Org. Chem. Jpn., 1991, 49, 205; M. Somei, T. Kawasaki, Y. Fukui, F. Yamada, T. Kobayashi, H. Aoyama, and D. Shinmyo, Heterocycles, 1992, 34, 1877; M. Somei and Y. Fukui, ibid., 1993, 36, 1859; M. Hasegawa, M. Tabata, K. Satoh, F. Yamada, and M. Somei, ibid., 1996, 43, 2333; Review: M. Somei, ibid., 1999, 50, 1157. See also reference 6b.
17. Review; M. Somei, J. Synth. Org. Chem. Jpn., 1991, 49, 205; M. Somei, T. Kawasaki, Y. Fukui, F. Yamada, T. Kobayashi, H. Aoyama, and D. Shinmyo, Heterocycles, 1992, 34, 1877; M. Somei and Y. Fukui, ibid., 1993, 36, 1859; M. Hasegawa, M. Tabata, K. Satoh, F. Yamada, and M. Somei, ibid., 1996, 43, 2333; Review: M. Somei, ibid., 1999, 50, 1157. See also reference 6b.
18. Review; M. Somei, J. Synth. Org. Chem. Jpn., 1991, 49, 205; M. Somei, T. Kawasaki, Y. Fukui, F. Yamada, T. Kobayashi, H. Aoyama, and D. Shinmyo, Heterocycles, 1992, 34, 1877; M. Somei and Y. Fukui, ibid., 1993, 36, 1859; M. Hasegawa, M. Tabata, K. Satoh, F. Yamada, and M. Somei, ibid., 1996, 43, 2333; Review: M. Somei, ibid., 1999, 50, 1157. See also reference 6b.
19. F. Yamada, Y. Fukui, D. Shinmyo, and M. Somei, Heterocycles, 1993, 35, 99; F. Yamada, D. Shinmyo, and M. Smei, ibid., 1994, 38, 273; M. Somei, F. Yamada, T. Izumi, and M. Nakajou, ibid., 1997, 45, 2327; M. Somei, A. Nakajou, T. Teramoto, A. Tanimoto, and F. Yamada, ibid., 1999, 51, 1949; M. Somei, A. Tanimoto, H. Orita, F. Yamada, and T. Ohta, ibid., 2001, 54, 425.
20. F. Yamada, Y. Fukui, D. Shinmyo, and M. Somei, Heterocycles, 1993, 35, 99; F. Yamada, D. Shinmyo, and M. Smei, ibid., 1994, 38, 273; M. Somei, F. Yamada, T. Izumi, and M. Nakajou, ibid., 1997, 45, 2327; M. Somei, A. Nakajou, T. Teramoto, A. Tanimoto, and F. Yamada, ibid., 1999, 51, 1949; M. Somei, A. Tanimoto, H. Orita, F. Yamada, and T. Ohta, ibid., 2001, 54, 425.
21. F. Yamada, Y. Fukui, D. Shinmyo, and M. Somei, Heterocycles, 1993, 35, 99; F. Yamada, D. Shinmyo, and M. Smei, ibid., 1994, 38, 273; M. Somei, F. Yamada, T. Izumi, and M. Nakajou, ibid., 1997, 45, 2327; M. Somei, A. Nakajou, T. Teramoto, A. Tanimoto, and F. Yamada, ibid., 1999, 51, 1949; M. Somei, A. Tanimoto, H. Orita, F. Yamada, and T. Ohta, ibid., 2001, 54, 425.
22. F. Yamada, Y. Fukui, D. Shinmyo, and M. Somei, Heterocycles, 1993, 35, 99; F. Yamada, D. Shinmyo, and M. Smei, ibid., 1994, 38, 273; M. Somei, F. Yamada, T. Izumi, and M. Nakajou, ibid., 1997, 45, 2327; M. Somei, A. Nakajou, T. Teramoto, A. Tanimoto, and F. Yamada, ibid., 1999, 51, 1949; M. Somei, A. Tanimoto, H. Orita, F. Yamada, and T. Ohta, ibid., 2001, 54, 425.
23. F. Yamada, Y. Fukui, D. Shinmyo, and M. Somei, Heterocycles, 1993, 35, 99; F. Yamada, D. Shinmyo, and M. Smei, ibid., 1994, 38, 273; M. Somei, F. Yamada, T. Izumi, and M. Nakajou, ibid., 1997, 45, 2327; M. Somei, A. Nakajou, T. Teramoto, A. Tanimoto, and F. Yamada, ibid., 1999, 51, 1949; M. Somei, A. Tanimoto, H. Orita, F. Yamada, and T. Ohta, ibid., 2001, 54, 425.
24. a) M. Somei and T. Kawasaki, Heterocycles, 1989, 29, 1251.
25. b) K. Yamada, T. Kawasaki, T. Fujita, and M. Somei, ibid., 2001, 55, 1151.
26. a) J. Kinjo, K. Yokomizo, Y. Awata, M. Shibata, and T. Nohara, Symposium Papers, 29th Symposium on the Chemistry of Natural Products, Sapporo, August 1987, p. 628.
27. b) R. M. Acheson, P. G. Hunt, D. M. Littlewood, B. A. Murrer, and H. E. Rosenberg, J. Chem. Soc., Perkin Trans. 1, 1978, 1117; M. Somei, H. Ohnishi, and Y. Shoken, Chem. Pharm. Bull., 1986, 34, 677. See also reference 6a.
28. b) R. M. Acheson, P. G. Hunt, D. M. Littlewood, B. A. Murrer, and H. E. Rosenberg, J. Chem. Soc., Perkin Trans. 1, 1978, 1117; M. Somei, H. Ohnishi, and Y. Shoken, Chem. Pharm. Bull., 1986, 34, 677. See also reference 6a.