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Synthesis of Substituted 1,2-Dihydro-2-imino-7-methyl-1,6(6H)-naphthyridin-5-ones (1997)

Ivanov, Ivo Christov ; Stoyanov, Edmont Vassilev ; Denkova, Pavletta Stoyanova ; [et al.]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1997 (1997), S. 1777-1781

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ISSN: 0947-3440

Keywords: 1,6-Naphthyridines ; 4-Aminopyridin-3-carbaldehydes ; Cyclizations ; Nitrogen heterocycles ; Antituberculosis agents ; Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Vilsmeier formylation of the 4-amino-2-pyridinones 4a-d leads to the formation of the corresponding 3-carbaldehydes 5a-d (the diformylated product 8 is isolated as a by-product). A cyclizing Knoevenagel reaction of 5 with CH-acidic nitriles 6 in the presence of piperidine gives substituted 2-imino-1,6(6H)-naphthyridin-5-ones 7a-p which have been shown by means of 1H-NMR and 1H-NOE measurements not to rearrange to 9. The products 7 are resistant against hydrolysis and only the ester group can be hydrolysed to an acid, 7q. Compounds 7c, d, f display in vitro antituberculosis activity.

Additional Material: 1 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/jlac.199719970822

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