A novel synthesis of 1,2,3,4-tetrahydroquinolines via Pummerer-type reaction of N-aryl-N-[(phenylsulfinyl)propyl]formamide

Chemical and Pharmaceutical Bulletin

Volumn 47, Issue 9, 1999, Pages 1269-1275

  Toda, Jun ^a   Sakagami, Michiya ^a   Sano, Takehiro ^a  

^a SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

1,2,3,4 tetrahydroquinoline; Pummerer reaction; Sulfoxide; Synthesis; Trifluoroacetic anhydride

Indexed keywords

1,2,3,4 TETRAHYDROQUINOLINE DERIVATIVE; ACID ANHYDRIDE; ANILINE DERIVATIVE; BENZOTHIAZEPINE DERIVATIVE; FORMAMIDE DERIVATIVE; SULFOXIDE; TRIFLUOROACETIC ACID;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0032872571     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.47.1269     Document Type: Article

References (16)

1. Some examples of pharmaceutical containing the TQ ring system: Baxter C. A. R., Richards H. C., J. Med. Chem., 14, 1033-1042 (1971); Hijikata A., Kikumoto R., Tonomura S., Hara H., Ninomiya K., Maruyama A., Sugano M., Tamao Y., Biochem. Biophys. Res. Commun., 101, 440-446 (1981); Uchida M., Chihiro M., Monta S., Kanbe T., Yamashita H., Yamasaki K., Yabuuchi Y., Nakagawa K., Chem. Pharm. Bull., 37, 2109-2116 (1989).
2. Some examples of pharmaceutical containing the TQ ring system: Baxter C. A. R., Richards H. C., J. Med. Chem., 14, 1033-1042 (1971); Hijikata A., Kikumoto R., Tonomura S., Hara H., Ninomiya K., Maruyama A., Sugano M., Tamao Y., Biochem. Biophys. Res. Commun., 101, 440-446 (1981); Uchida M., Chihiro M., Monta S., Kanbe T., Yamashita H., Yamasaki K., Yabuuchi Y., Nakagawa K., Chem. Pharm. Bull., 37, 2109-2116 (1989).
3. Some examples of pharmaceutical containing the TQ ring system: Baxter C. A. R., Richards H. C., J. Med. Chem., 14, 1033-1042 (1971); Hijikata A., Kikumoto R., Tonomura S., Hara H., Ninomiya K., Maruyama A., Sugano M., Tamao Y., Biochem. Biophys. Res. Commun., 101, 440-446 (1981); Uchida M., Chihiro M., Monta S., Kanbe T., Yamashita H., Yamasaki K., Yabuuchi Y., Nakagawa K., Chem. Pharm. Bull., 37, 2109-2116 (1989).
4. The reaction of epichlorohydrin with some aromatic amines yielded TQs, but in low yields. [Davis W., Savige W. E., J. Chem. Soc., 1950, 890-894].
5. "Houben-Weyl, Methoden der Organischen Chemie," Band 11/11, ed. by Muller E., Bayer O., Georg Thieme Verlag Stuttgart, 1957, pp. 698-699 and 715-730.
6. a) Cribble G. W., Heald P. W., Synthesis, 1975, 650-651;
7. b) Murahashi S., Imada Y., Hirai Y., Bull. Chem. Soc. Jpn., 62, 2968-2976 (1989).
8. "Houben-Weyl, Methoden der Organischen Chemie," Band E7a, Hetarene II-Teil 1, ed. by Kreher R. P., 1991, Georg Thieme Verlag Stuttgart, New York, pp. 290-571.
9. a) Shinohara T., Toda J., Sano T., Chem. Pharm. Bull., 45, 813-819 (1997);
10. b) Shinohara T., Takeda A., Toda J., Ueda Y., Kohno M., Sano T., ibid., 46, 918-927 (1998).
11. Shinohara T., Takeda A., Toda J., Terasawa N., Sano T., Heterocycles, 46, 555-565 (1997); Shinohara T., Takeda A., Toda J., Sano T., ibid., 48, 981-992 (1998).
12. Shinohara T., Takeda A., Toda J., Terasawa N., Sano T., Heterocycles, 46, 555-565 (1997); Shinohara T., Takeda A., Toda J., Sano T., ibid., 48, 981-992 (1998).
13. Shinohara T., Takeda A., Toda J., Sano T., Chem. Pharm. Bull., 46, 430-433 (1998).
14. Kirner W. R., Richter G. H., J. Am. Chem. Soc., 51, 3409-3418 (1929).
15. Levitz M., Borgert M. T., J. Org. Chem., 10, 341-346 (1945).
16. Nizar P. N. H., Chauhan S. M. S., Indian J. Chem. Sect B, 29, 984-985 (1990).