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Regioselective substitution of 6,7-dichloroquinoline-5,8-dione: synthesis and X-ray crystal structure of 4a,10,11-triazabenzo[3,2-a]fluorene-5,6-diones
- Source :
-
Bioorganic & Medicinal Chemistry . Apr2002, Vol. 11 Issue 8, p1829. 5p. - Publication Year :
- 2003
-
Abstract
- 6,7-Dichloroquinoline-5,8-dione (1) was reacted with a number of 2-aminopyridine derivatives. Of the several possible products of this reaction, 4a,10,11-triazabenzo[3,2-a]fluorene-5,6-dione (6), produced by condensation and rearrangement, was obtained as the major product, and its structure was subsequently unambigously determined by X-ray crystallographic study. Ortho-quinones were produced via nucleophilic substitution at position C7, which was unexpected, considering that para-quinones were produced via C6 substitution in the reaction between compound 1 and ethyl acetoacetate in our previous work. Such unexpected nucleophilic substitution at C7 provides an effective, yet simple route, to the preparation of biologically active ortho-quinone derivatives. [Copyright &y& Elsevier]
- Subjects :
- *QUINOLINE
*PYRIDINE
Subjects
Details
- Language :
- English
- ISSN :
- 09680896
- Volume :
- 11
- Issue :
- 8
- Database :
- Academic Search Index
- Journal :
- Bioorganic & Medicinal Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 9440671
- Full Text :
- https://doi.org/10.1016/S0968-0896(02)00667-3