New synthesis of pyridoacridines based on an intramolecular aza-Diels-Alder reaction followed by an unprecedented rearrangement

Chemical Communications

Volumn , Issue 17, 1999, Pages 1721-1722

  Cuerva, Juan M ^a   Cárdenas, Diego J ^a   Echavarren, Antonio M ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOQUINONE; ACRIDINE DERIVATIVE; ASCIDIDEMIN; HYDRAZONE DERIVATIVE; PYRIDOACRIDINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 0342659530     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a905234h     Document Type: Article

References (30)

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2. (b) 2-bromoascididemin (2-bromoleptoclidinininone): J. J. Bloor and F. J. Schmitz, J. Am. Chem. Soc. 1987, 109, 6134; 11-Hidroxyascididemin
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7. -1, respectively).
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11. The first step of a synthesis of the alkaloid meridine is a Diels-Alder cycloaddition of the nitro analogue of 3 which proceeds in low yield (6%): Y. Kitahara, F. Tamura and A. Kubo, Chem. Pharm. Bull. 1994, 42, 1363; S. Nakahara, Y. Tanaka and A. Kubo, Heterocycles, 1996, 43, 2113; a similar reaction was used for the synthesis of cistodamine: Y. Kitahara, F. Tamura and A. Kubo, Tetrahedron Lett. 1997, 38, 4441. Alternative synthesis of aromatized adducts: P. Molina, A. Pastor and M. Villaplana, Tetrahedron 1995, 51, 1265.
12. The first step of a synthesis of the alkaloid meridine is a Diels-Alder cycloaddition of the nitro analogue of 3 which proceeds in low yield (6%): Y. Kitahara, F. Tamura and A. Kubo, Chem. Pharm. Bull. 1994, 42, 1363; S. Nakahara, Y. Tanaka and A. Kubo, Heterocycles, 1996, 43, 2113; a similar reaction was used for the synthesis of cistodamine: Y. Kitahara, F. Tamura and A. Kubo, Tetrahedron Lett. 1997, 38, 4441. Alternative synthesis of aromatized adducts: P. Molina, A. Pastor and M. Villaplana, Tetrahedron 1995, 51, 1265.
13. The first step of a synthesis of the alkaloid meridine is a Diels-Alder cycloaddition of the nitro analogue of 3 which proceeds in low yield (6%): Y. Kitahara, F. Tamura and A. Kubo, Chem. Pharm. Bull. 1994, 42, 1363; S. Nakahara, Y. Tanaka and A. Kubo, Heterocycles, 1996, 43, 2113; a similar reaction was used for the synthesis of cistodamine: Y. Kitahara, F. Tamura and A. Kubo, Tetrahedron Lett. 1997, 38, 4441. Alternative synthesis of aromatized adducts: P. Molina, A. Pastor and M. Villaplana, Tetrahedron 1995, 51, 1265.
14. The first step of a synthesis of the alkaloid meridine is a Diels-Alder cycloaddition of the nitro analogue of 3 which proceeds in low yield (6%): Y. Kitahara, F. Tamura and A. Kubo, Chem. Pharm. Bull. 1994, 42, 1363; S. Nakahara, Y. Tanaka and A. Kubo, Heterocycles, 1996, 43, 2113; a similar reaction was used for the synthesis of cistodamine: Y. Kitahara, F. Tamura and A. Kubo, Tetrahedron Lett. 1997, 38, 4441. Alternative synthesis of aromatized adducts: P. Molina, A. Pastor and M. Villaplana, Tetrahedron 1995, 51, 1265.
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21. By using the reaction pathway outlined in Scheme 2, adducts 5d-e could be converted into 11-hydroxyascididemin (1c).
22. Yield based on unrecovered starting material.
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26. 6-TFA-d solution, sealed NMR tube). In addition, a small signal at 1.8 ppm attributable to dissolved acetylene was also observed.
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30. The methoxime and diphenylhydrazone analogues of 5a afforded 7a after being treated with TFA.