Intramolecular [4 + 2] cycloaddition reactions of ketenimines: A new synthesis of benz[b]acridines

Synthesis

Volumn , Issue 16, 2002, Pages 2393-2398

  Alajarín, Mateo ^a   Vidal, Angel ^a   Ortín, María Mar ^a   Tovar, Fulgencio ^a  

^a UNIVERSITY OF MURCIA   (Spain)

Author keywords

Acridines; Azides; Cycloadditions; Ketenimines; Phosphazenes; Polycycles

Indexed keywords

CHEMICAL REACTIONS; OXIDATION;

CYCLOADDITION REACTION;

AROMATIC COMPOUNDS;

ACRIDINE DERIVATIVE; BENZ[B]ACRIDINE DERIVATIVE; KETENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; INFRARED SPECTROSCOPY; OXIDATION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0036437455     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-35234     Document Type: Article

References (23)

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7. General syntheses of benz[b]acridines have been scarcely reported and usually yield oxidized derivatives. For examples, see: (a) Narasimhan, N. S.; Ranade, A. C. Indian J. Chem. 1969, 7, 538. (b) Roushdi, I. M.; Mikhail, A. A.; Chaaban, I. Pharmazie 1976, 31, 406. (c) Joos, K.; Pardo, M.; Schäfer, W. J. Chem. Res., Synop. 1978, 406. (d) Hamdan, A. J.; Moore, H. W. J. Org. Chem. 1985, 50, 3427. (e) Chuang, C.-P.; Wu, Y.-L.; Jiang, M.-C. Tetrahedron 1999, 55, 11229. (f) Prato, M.; Scorrano, G.; Stiranello, M.; Tecilla, P.; Lucchini, V. Gazz. Chim. Ital. 1987, 117, 325. (g) Alvarez, M.; Ajana, W.; López-Calahorra, F.; Joule, J. A. J. Chem. Soc., Perkin Trans. 1 1994, 917.
8. General syntheses of benz[b]acridines have been scarcely reported and usually yield oxidized derivatives. For examples, see: (a) Narasimhan, N. S.; Ranade, A. C. Indian J. Chem. 1969, 7, 538. (b) Roushdi, I. M.; Mikhail, A. A.; Chaaban, I. Pharmazie 1976, 31, 406. (c) Joos, K.; Pardo, M.; Schäfer, W. J. Chem. Res., Synop. 1978, 406. (d) Hamdan, A. J.; Moore, H. W. J. Org. Chem. 1985, 50, 3427. (e) Chuang, C.-P.; Wu, Y.-L.; Jiang, M.-C. Tetrahedron 1999, 55, 11229. (f) Prato, M.; Scorrano, G.; Stiranello, M.; Tecilla, P.; Lucchini, V. Gazz. Chim. Ital. 1987, 117, 325. (g) Alvarez, M.; Ajana, W.; López-Calahorra, F.; Joule, J. A. J. Chem. Soc., Perkin Trans. 1 1994, 917.
9. General syntheses of benz[b]acridines have been scarcely reported and usually yield oxidized derivatives. For examples, see: (a) Narasimhan, N. S.; Ranade, A. C. Indian J. Chem. 1969, 7, 538. (b) Roushdi, I. M.; Mikhail, A. A.; Chaaban, I. Pharmazie 1976, 31, 406. (c) Joos, K.; Pardo, M.; Schäfer, W. J. Chem. Res., Synop. 1978, 406. (d) Hamdan, A. J.; Moore, H. W. J. Org. Chem. 1985, 50, 3427. (e) Chuang, C.-P.; Wu, Y.-L.; Jiang, M.-C. Tetrahedron 1999, 55, 11229. (f) Prato, M.; Scorrano, G.; Stiranello, M.; Tecilla, P.; Lucchini, V. Gazz. Chim. Ital. 1987, 117, 325. (g) Alvarez, M.; Ajana, W.; López-Calahorra, F.; Joule, J. A. J. Chem. Soc., Perkin Trans. 1 1994, 917.
10. General syntheses of benz[b]acridines have been scarcely reported and usually yield oxidized derivatives. For examples, see: (a) Narasimhan, N. S.; Ranade, A. C. Indian J. Chem. 1969, 7, 538. (b) Roushdi, I. M.; Mikhail, A. A.; Chaaban, I. Pharmazie 1976, 31, 406. (c) Joos, K.; Pardo, M.; Schäfer, W. J. Chem. Res., Synop. 1978, 406. (d) Hamdan, A. J.; Moore, H. W. J. Org. Chem. 1985, 50, 3427. (e) Chuang, C.-P.; Wu, Y.-L.; Jiang, M.-C. Tetrahedron 1999, 55, 11229. (f) Prato, M.; Scorrano, G.; Stiranello, M.; Tecilla, P.; Lucchini, V. Gazz. Chim. Ital. 1987, 117, 325. (g) Alvarez, M.; Ajana, W.; López-Calahorra, F.; Joule, J. A. J. Chem. Soc., Perkin Trans. 1 1994, 917.
11. General syntheses of benz[b]acridines have been scarcely reported and usually yield oxidized derivatives. For examples, see: (a) Narasimhan, N. S.; Ranade, A. C. Indian J. Chem. 1969, 7, 538. (b) Roushdi, I. M.; Mikhail, A. A.; Chaaban, I. Pharmazie 1976, 31, 406. (c) Joos, K.; Pardo, M.; Schäfer, W. J. Chem. Res., Synop. 1978, 406. (d) Hamdan, A. J.; Moore, H. W. J. Org. Chem. 1985, 50, 3427. (e) Chuang, C.-P.; Wu, Y.-L.; Jiang, M.-C. Tetrahedron 1999, 55, 11229. (f) Prato, M.; Scorrano, G.; Stiranello, M.; Tecilla, P.; Lucchini, V. Gazz. Chim. Ital. 1987, 117, 325. (g) Alvarez, M.; Ajana, W.; López-Calahorra, F.; Joule, J. A. J. Chem. Soc., Perkin Trans. 1 1994, 917.
12. General syntheses of benz[b]acridines have been scarcely reported and usually yield oxidized derivatives. For examples, see: (a) Narasimhan, N. S.; Ranade, A. C. Indian J. Chem. 1969, 7, 538. (b) Roushdi, I. M.; Mikhail, A. A.; Chaaban, I. Pharmazie 1976, 31, 406. (c) Joos, K.; Pardo, M.; Schäfer, W. J. Chem. Res., Synop. 1978, 406. (d) Hamdan, A. J.; Moore, H. W. J. Org. Chem. 1985, 50, 3427. (e) Chuang, C.-P.; Wu, Y.-L.; Jiang, M.-C. Tetrahedron 1999, 55, 11229. (f) Prato, M.; Scorrano, G.; Stiranello, M.; Tecilla, P.; Lucchini, V. Gazz. Chim. Ital. 1987, 117, 325. (g) Alvarez, M.; Ajana, W.; López-Calahorra, F.; Joule, J. A. J. Chem. Soc., Perkin Trans. 1 1994, 917.
13. General syntheses of benz[b]acridines have been scarcely reported and usually yield oxidized derivatives. For examples, see: (a) Narasimhan, N. S.; Ranade, A. C. Indian J. Chem. 1969, 7, 538. (b) Roushdi, I. M.; Mikhail, A. A.; Chaaban, I. Pharmazie 1976, 31, 406. (c) Joos, K.; Pardo, M.; Schäfer, W. J. Chem. Res., Synop. 1978, 406. (d) Hamdan, A. J.; Moore, H. W. J. Org. Chem. 1985, 50, 3427. (e) Chuang, C.-P.; Wu, Y.-L.; Jiang, M.-C. Tetrahedron 1999, 55, 11229. (f) Prato, M.; Scorrano, G.; Stiranello, M.; Tecilla, P.; Lucchini, V. Gazz. Chim. Ital. 1987, 117, 325. (g) Alvarez, M.; Ajana, W.; López-Calahorra, F.; Joule, J. A. J. Chem. Soc., Perkin Trans. 1 1994, 917.
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18. 3): δ = 1.29.
19. The heating of the toluene solutions of the ketenimines 10 at 130°C in a sealed tube gave mixtures of 5,11,11a,12-tetrahydro, 5,12-dihydro and the fully aromatic 11-aryl-6-phenylbenz[b]acridines, and the same results were obtained when this thermal treatment was carried out in the presence of Pd/C.
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