Tandem 1,3-Dipolar Cycloadditions of Pyridinium or Isoquinolinium Methylides with Olefinic Dipolarophiles Leading to Cycl[3.2.2]azines. “Enamine Route” as a New Generation Method of Azomethine Ylides

Journal of Organic Chemistry

Volumn 54, Issue 2, 1989, Pages 420-424

  Kanemasa, Shuji ^a   Takenaka, Shigeori ^a   Watanabe, Haruyuki ^a   Tsuge, Otohiko ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000028624     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00263a030     Document Type: Article

References (5)

1. Krohnke, F. Ber. Deutsch. Chem. Ges. 1935,68,1177. See also the following reviews: Stuckwisch, C. G. Synthesis 1973, 469. Surpateanu, G; Lablache-Combier, A. Heterocycles 1984,22, 2079. N-Ylid Chemistry; Zugravescu; I., Petrovanu, M., Eds.; McGraw-Hill International: New York, 1976.
2. Tsuge, O.; Kanemasa, S.; Takenaka, S. Heterocycles 1983, 20, 1907. (b) Tsuge, O.; Kanemasa, S.; Takenaka, S. Chem. Lett. 1985, 355. (c) Tsuge, O.; Kanemasa, S.; Takenaka, S. Bull. Chem. Soc. Jpn. 1985, 58, 3137. (d) Tsuge, O.; Kanemasa, S.; Takenaka, S. Ber. Deutsch. Chem. Ges. 1985, 58, 3320.
3. Tsuge, O.; Kanemasa, S.; Kuraoka, S.; Takenaka, S. Chem. Lett. 1984, 281. (b) Miki, Y.; Hachiken, H.; Takemura, S. Heterocycles 1984, 22, 701. (c) Tsuge, O.; Kanemasa, S.; Takenaka, S. Chem. Lett. 1984,465. (d) Tsuge, O.; Kanemasa, S.; Takenaka, S. Bull. Chem. Soc. Jpn. 1987, 60, 1489.
4. Condensations of α-anino esters, nitriles, or acids with carbonyl compounds generating azomethine ylides are believed to occur via the corresponding iminium intermediates: (a) Tsuge, O.; Ueno, K.; Kanemasa, S.; Yorozu, K. Bull. Chem. Soc. Jpn. 1986,59,1809. (b) Confalone, P. N.; Huie, E. M. J. Org. Chem. 1983,48, 2994. (c) Tsuge, O.; Kanemasa, S.; Ohe, M.; Yorozu, K.; Takenaka, S.; Ueno, K. Bull. Chem. Soc. Jpn. 1987, 60, 4067. (d) Grigg, R.; Thianpatanagul, S. J. Chem. Soc., Chem. Commun. 1984, 180. (e) Tsuge, O.; Kanemasa, S.; Ohe, M.; Takenaka, S. Bull. Chem. Soc. Jpn. 1987, 60, 4079.
5. Spontaneous deprotonation occurs at the a-position of iminium salts when the a-hydrogen is activated by an electron-withdrawing substituent: Grigg, R.; Kemp, J. J. Chem. Soc., Chem. Commun. 1978, 109.