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Volumn 61, Issue 3, 1996, Pages 1155-1158

Concise syntheses of the novel 1H-pyrrolo[3,2-g]quinazoline ring system and its [2,3-f] angular isomer

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLE DERIVATIVE; PYRROLO[2,3 F]QUINAZOLINE DERIVATIVE; PYRROLO[3,2 G]QUINAZOLINE DERIVATIVE; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0001460085     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951790b     Document Type: Article
Times cited : (28)

References (40)
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    • Imidazo[4,5-f]quinazolines: (a) Morrice, A. G.; Sprecker, M. A.; Leonard, N. J. J. Org. Chem. 1975, 40, 363-366. (b) Schneller, S. W.; Ibay, A. C. J. Org. Chem. 1986, 51, 4067-4070. Imidazo[4,5-h]-quinazolines: (c) ref 2a.
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    • Imidazo[4,5-f]quinazolines: (a) Morrice, A. G.; Sprecker, M. A.; Leonard, N. J. J. Org. Chem. 1975, 40, 363-366. (b) Schneller, S. W.; Ibay, A. C. J. Org. Chem. 1986, 51, 4067-4070. Imidazo[4,5-h]-quinazolines: (c) ref 2a.
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    • Imidazo[4,5-h]-quinazolines: (c) ref 2a
    • Imidazo[4,5-f]quinazolines: (a) Morrice, A. G.; Sprecker, M. A.; Leonard, N. J. J. Org. Chem. 1975, 40, 363-366. (b) Schneller, S. W.; Ibay, A. C. J. Org. Chem. 1986, 51, 4067-4070. Imidazo[4,5-h]-quinazolines: (c) ref 2a.
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    • Pyrazolo[3,4-g]quinazolines: (a) Lichtenthaler, F. W.; Moser, A. Tetrahedron Lett. 1981, 22, 4397-4400. Pyrazolo[4,3-g]quinazolines: (b) Foster, R. H.; Leonard, N. J. J. Org. Chem. 1979, 44, 4609-4611. (c) Cuny, E.; Lichtenthaler, F. W.; Moser, A. Tetrahedron Lett. 1980, 21, 3029-3032. (d) Cuny, E.; Lichtenthaler, F. W.; Jahn, U. Chem. Ber. 1981, 114, 1624-1635.
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    • Pyrazolo[3,4-g]quinazolines: (a) Lichtenthaler, F. W.; Moser, A. Tetrahedron Lett. 1981, 22, 4397-4400. Pyrazolo[4,3-g]quinazolines: (b) Foster, R. H.; Leonard, N. J. J. Org. Chem. 1979, 44, 4609-4611. (c) Cuny, E.; Lichtenthaler, F. W.; Moser, A. Tetrahedron Lett. 1980, 21, 3029-3032. (d) Cuny, E.; Lichtenthaler, F. W.; Jahn, U. Chem. Ber. 1981, 114, 1624-1635.
    • (1979) J. Org. Chem. , vol.44 , pp. 4609-4611
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    • Pyrazolo[3,4-g]quinazolines: (a) Lichtenthaler, F. W.; Moser, A. Tetrahedron Lett. 1981, 22, 4397-4400. Pyrazolo[4,3-g]quinazolines: (b) Foster, R. H.; Leonard, N. J. J. Org. Chem. 1979, 44, 4609-4611. (c) Cuny, E.; Lichtenthaler, F. W.; Moser, A. Tetrahedron Lett. 1980, 21, 3029-3032. (d) Cuny, E.; Lichtenthaler, F. W.; Jahn, U. Chem. Ber. 1981, 114, 1624-1635.
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    • Pyrazolo[3,4-g]quinazolines: (a) Lichtenthaler, F. W.; Moser, A. Tetrahedron Lett. 1981, 22, 4397-4400. Pyrazolo[4,3-g]quinazolines: (b) Foster, R. H.; Leonard, N. J. J. Org. Chem. 1979, 44, 4609-4611. (c) Cuny, E.; Lichtenthaler, F. W.; Moser, A. Tetrahedron Lett. 1980, 21, 3029-3032. (d) Cuny, E.; Lichtenthaler, F. W.; Jahn, U. Chem. Ber. 1981, 114, 1624-1635.
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  • 12
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    • Pyrazolo[3,4-h]quinazolines: (a) ref 3a
    • Pyrazolo[3,4-h]quinazolines: (a) ref 3a; Pyrazolo[4,3-f]-quinazolines: (b) ref 3d; Pyrazolo[3,4-f]quinazolines: (c) ref 3c. (d) Foster, R. H.; Leonard, N. J. J. Org. Chem. 1980, 45, 3072-3077. (e) Lichtenthaler, F. W.; Cuny, E. Heterocycles 1981, 15, 1053-1059.
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    • Pyrazolo[4,3-f]-quinazolines: (b) ref 3d
    • Pyrazolo[3,4-h]quinazolines: (a) ref 3a; Pyrazolo[4,3-f]-quinazolines: (b) ref 3d; Pyrazolo[3,4-f]quinazolines: (c) ref 3c. (d) Foster, R. H.; Leonard, N. J. J. Org. Chem. 1980, 45, 3072-3077. (e) Lichtenthaler, F. W.; Cuny, E. Heterocycles 1981, 15, 1053-1059.
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    • Pyrazolo[3,4-f]quinazolines: (c) ref 3c.
    • Pyrazolo[3,4-h]quinazolines: (a) ref 3a; Pyrazolo[4,3-f]-quinazolines: (b) ref 3d; Pyrazolo[3,4-f]quinazolines: (c) ref 3c. (d) Foster, R. H.; Leonard, N. J. J. Org. Chem. 1980, 45, 3072-3077. (e) Lichtenthaler, F. W.; Cuny, E. Heterocycles 1981, 15, 1053-1059.
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    • Pyrazolo[3,4-h]quinazolines: (a) ref 3a; Pyrazolo[4,3-f]-quinazolines: (b) ref 3d; Pyrazolo[3,4-f]quinazolines: (c) ref 3c. (d) Foster, R. H.; Leonard, N. J. J. Org. Chem. 1980, 45, 3072-3077. (e) Lichtenthaler, F. W.; Cuny, E. Heterocycles 1981, 15, 1053-1059.
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    • Pyrazolo[3,4-h]quinazolines: (a) ref 3a; Pyrazolo[4,3-f]-quinazolines: (b) ref 3d; Pyrazolo[3,4-f]quinazolines: (c) ref 3c. (d) Foster, R. H.; Leonard, N. J. J. Org. Chem. 1980, 45, 3072-3077. (e) Lichtenthaler, F. W.; Cuny, E. Heterocycles 1981, 15, 1053-1059.
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    • note
    • 13C NMR spectrum, there are additional resonances at δ 132.96, 122.93, 100.02, 59.64 and 16.26. The 132.96 and 100.02 signals are the most prominent, and correspond to CH carbons from the DEPT spectrum. Therefore, they most likely correspond to C-2 and C-3, respectively, of 18.
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    • Albert, A. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic: New York, 1982; Vol 32, pp 1-81.
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    • note
    • It is imperative to use pure (tert-butyloxy)bis(dimethylamino)-methane in this reaction. In one run utilizing old reagent, the reaction did not proceed cleanly. Attempted purification of crude 20 by column chromatography resulted in significant decomposition, in part to amide 21.
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    • note
    • -, 40), 175 (100), 174 (43).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.