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SYNTHESIS OF 3,13-DICHLOROBENZO[b]QUINO[4,3-h][1,6]NAPHTHYRIDIN-6(5H)-ONE DERIVATIVES FROM 2-OXOQUINOLINE-3-CARBONYL CHLORIDE AND 2,6-DICHLOROQUINOLIN-4-AMINE

Adhiyaman Kottai Munusamy Magesh Selva Kumar, Subramanian Parameswaran Rajendran, Selvaraj Mohana Roopan
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Abstract


The reaction of 2-oxo-1,2-dihydroquinoline-3-carbonyl chlorides and 2,6-dichloroquinolin-4-amine leads to the formation of N-(2,6-dichloroquinolin-4-yl)-2-oxo-1,2-dihydroquinoline-3-carboxamides. The latter is cyclized to fused [1,6]naphthyridine derivative – 3,13-dichlorobenzo[b]quino[4,3-h][1,6]naphthyridin-6(5H)-one, under heating in polyphosphoric acid at 150°C. The reaction sequence was generalized and was extended to synthetic derivatives. The structures of all synthesized compounds were confirmed by spectral data and elemental analysis.

How to Cite
Magesh Selva Kumar, A. K. M.; Rajendran, S. P.; Mohana Roopan, S. Chem. Heterocycl. Compd. 2015, 51, 346. [Khim. Geterotsikl. Soedin. 2015, 51, 346.]

For this article in the English edition see DOI 10.1007/s10593-015-1706-5

 


Keywords


2-chloroquinoline-3-carbaldehyde; 2,6-dichloroquinolin-4-amine; N-(quinolin-4-yl)-2-oxo-1,2-dihydroquinoline-3-carboxamide; benzo[b]quino[4,3-h][1,6]naphthyridin-6(5H)-one

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