A simple synthesis of dibenzo[b,g][1,8]naphthyridines

Article abstract of DOI:10.1081/SCC-120037914

2-Chloro-3-formyl quinoline and its derivatives on reaction with anilines in DMF afforded the dibenzo[b,g][1,8]naphthyridines.

Full text of DOI:10.1081/SCC-120037914

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A Simple Synthesis of Dibenzo[b,g]
[
1,8]naphthyridines
a
a
a
N. Sampathkumar , N. Venkatesh Kumar & S. P. Rajendran
a
Department of Chemistry, Bharathiar University, Coimbatore, Tamil Nadu, 641046, India
Version of record first published: 20 Aug 2006.
To cite this article: N. Sampathkumar, N. Venkatesh Kumar & S. P. Rajendran (2004): A Simple Synthesis of Dibenzo[b,g]
[1,8]naphthyridines, Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic
Chemistry, 34:11, 2019-2024
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SYNTHETIC COMMUNICATIONS
Vol. 34, No. 11, pp. 2019–2024, 2004
A Simple Synthesis of
Dibenzo[b,g][1,8]naphthyridines
N. Sampathkumar, N. Venkatesh Kumar, and
S. P. Rajendran*
Department of Chemistry, Bharathiar University,
Coimbatore, Tamil Nadu, India
ABSTRACT
2-Chloro-3-formyl quinoline and its derivatives on reaction with anilines
in DMF afforded the dibenzo[b,g][1,8]naphthyridines.
KeyWords: Dibenzo[b,g][1,8]naphthyridines; Anilines; 2-Chloro-3-formyl
quinolines; DMF.
INTRODUCTION
Interesting pharmacological properties have been associated with
[
1–4]
[
reports on the synthesis of dibenzo[b,g][1,8]naphthyridines by the reaction
1,8]naphthyridine and its derivatives.
Available literature showed the
*
Correspondence: S. P. Rajendran, Department of Chemistry, Bharathiar University,
Coimbatore, Tamil Nadu 641046, India; E-mail: rajendransp@yahoo.com.
2
019
DOI: 10.1081/SCC-120037914
0039-7911 (Print); 1532-2432 (Online)
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Copyright # 2004 by Marcel Dekker, Inc.

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020
Sampathkumar, Venkatesh Kumar, and Rajendran
[5]
of dimethyl bis(methylthio)methylene malonate with anilines. Kidwai and
[
6]
Kohli synthesised dibenzo[b,g]-5-methyl-1,8-naphthyridines in a three-
step process from 2-hydroxy-4-methyl quinoline and aniline. Recently, we
have reported the synthesis of 1,2,3,4-tetrahydro dibenzo[b,g][1,8]naphthyri-
[
7]
dines from 2-amino-3-formyl quinoline and cyclohexanone.
RESULTS AND DISCUSSION
The reaction of 2-chloro-3-formyl-quinoloine with aniline was attempted
1
in DMF at 758C. The resulting product was analysed by IR, H NMR, mass
spectroscopy, and elemental analysis and assigned the structure dibenzo
[b,g][1,8]naphthyridine. A number of 2-chloro-3-formyl-quinolines were
reacted with aniline to produce substituted dibenzo[b,g][1,8]naphthyridines,
which revealed the generality of this protocol (Sch. 1).
EXPERIMENTAL SECTION
Melting points were determined on a Boetius microheating table and are
uncorrected. Thin-layer chromatography were performed on glass plates
coated with silica gel-G incorporating 13% CaSO as binder. IR spectra
4
were recorded on a Perkin–Elmer-597 infrared spectrophotometer as KBr
1
pellets. H NMR spectra were recorded on an AMX-400 MHz NMR spectro-
photometer using Me Si as internal standard and chemical shifts are quoted in
4
ppm. Mass spectra were recorded on an Autospec mass spectrophotometer.
Elemental analyses were performed by Cario-Elmer 1106 and Perkin–
Elmer analyser.
1 2 3 4
Scheme 1. (i) Aniline, DMF, 758C/stirring, 2 hr; (a) R 55 R 55 R 55 R 55 H; (b)
R 55 R 55 H, R 55 CH , R 55 H; (c) R 55 CH , R 55 R 55 R 55 H; (d) R 55 CH , R 55 H,
2
1
2
3
3
4
1
3
2
3
4
1
3
R
R
3
55 CH
3
, R
4
55 H; (e) R
55 OCH
1
55 R
2
55 H, R
55 R
3
55 OCH
55 R
3
, R
4
55 H; (f) R
55 OCH
1
55 H, R
2
55 OCH
3
,
55 R 55 H; (g)
3 4
R
1
3
,
R
2
3
4
55 H; (h)
R
1
3
,
R
2
55 R 55 H,
3
R 55 OCH ; (i) R 55 2 CH 55 CH 2 CH 55 CH 2 R , R 55 R 55 H.
3
4
3
1
2
4

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Dibenzo[b,g][1,8]naphthyridines
2021
d

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022
Sampathkumar, Venkatesh Kumar, and Rajendran
d

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Dibenzo[b,g][1,8]naphthyridines
2023
2
-Chloro-3-formyl-quinolines
(1a–i). 2-Chloro-3-formyl-quinoline
derivatives were synthesised by Vilsmeier–Haack reaction of acetanilide
[
8]
with POCl /DMF.
3
Dibenzo[b,g][1,8]naphthyridines (2). Compound 1 (0.01 mol), aniline
0.0125 mol) in DMF (20 mL) were stirred at (758C) for 2 hr. The reaction
(
was monitored by TLC. DMF was removed under reduced pressure, the residue
washed with 2 N NaOH solution (50 mL), water and then chromatographed on
silica gel (60–120) using light petroleum–ethyl acetate (98 : 2) as eluant to
give 2 (86%), recrystallised from ethyl acetate–light petroleum (Table 1).
ACKNOWLEDGMENTS
We thank the services rendered by the “Sophisticated Instrumentation
Facility” at Indian Institute of science, Bangalore, “Indian Institute of Chemi-
1
cal Technology,” Hyderabad in recording the H NMR and mass spectra.
REFERENCES
1
. Lowe, P.A. Naphthyridines pyridoquinolines, anthyridines and similar
compounds. In Comprehensive Heterocyclic Chemistry, Part 2A; Six Mem-
bered Rings with One Nitrogen Atom; Pregamon Press: New York, 1984;
Vol. 2, 581–627.
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3
4
5
. Ferrarini, P.L.;Mori, C.;Badwneh, M.;Calderone, V.;Calzolari, L.;Loffredo, T.;
Martinotti, E.; Saccomanni, G. Synthesis of 1,8-naphthyridine derivatives:poten-
tial antihypertensive agents—part 7. Eur. J. Med. Chem. 1998, 33, 383–387.
. Ferrani, P.L.; Manera, C.; Mori, C.; Badwneh, M.; Saccomanni, G.
Synthesis and evaluation of antimycobacterial activity of 4-phenyl-
1,8-naphthyridine derivatives. IL Farmaco 1998, 53, 741–746.
. Nyce, P.L.; Gala, D.; Steinman, M. An efficient synthesis of 1,8-naph-
thyridin-2(1H)-ones: synthesis of leukotriene inhibitors SCH 37244.
Synthesis 1991, 7, 571–574.
. Tominaga, Y.; Michioka, T.; Moriyama, K.; Hosomi, A. Synthesis of qui-
noline derivatives using ketene dithioacetal. J. Heterocyclic. Chem. 1990,
27, 1217–1225.
6
7
. Kidwai, M.; Kohli, S. Synthesis of dibenzo(b,g)-5-methyl-1,8-naphthyri-
dines. Indian J. Chem. 2001, 40B, 248–249.
. Prakash, G.A.; Rajendran, S.P. Synthesis of 1,2,3,4-tetrahydro dibenzo
[
b,g][1,8]naphthyridines. Heterocyclic Commun. 2000, 6 (1), 63–66.

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Sampathkumar, Venkatesh Kumar, and Rajendran
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. Meth-Cohn, O.; Narine, B.; Tarnowski, B. A versatile new synthesis of
quinolines and related fused pyridines. Part-5. The synthesis of 2-chloro-
quinoline-3-carbaldehydes. J. Chem. Soc. Perkin Trans-I 1981,
1520–1530.
Received in India January 5, 2004

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