164
Naser Montazeri and Elnaz Mohammad Nezhad
1
physical constants (m.p.), IR and H NMR spectroscopy and comparison with authentic
samples.
1
Representative IR and H NMR spectral data for the selected products. 1,2-Dihydro-1-(4-
o
chlorophenyl)naphtho[1,2-][1,3]oxazine-3-one (4a): m.p. = 218–220 C; IR (KBr): 3224, 3146,
1
1
8
=
734 cm–1; H NMR (300 MHz, DMSO- d ): δ = 5.83 (s, 1 H, CH), 6.9–7.6 (m, 10 H, Ar–H),
6
.49 (s, 1 H, NH). 1,2-Dihydro-1-(2-chlorophenyl)naphtho[1,2-e][1,3] oxazine-3-one (4h): m.p.
253 C; IR(KBr): 3237, 3124, 1727 cm ; H NMR (300 MHz, DMSO-d ): δ = 6.50 (d, 1H,
o
-1 1
6
J = 2.94, CH), 7.18-8.01 (m, 10H, Ar-H), 8.89 (s, 1H, NH).
CONCLUSION
In conclusion, we have described a highly efficient one-pot synthesis for the preparation of
naphthoxazine-3-one derivatives in three-component cyclocondensation reaction of 2-naphtol,
aromatic aldehydes and urea under solvent-free conditions. Easy work-up, low cost, ready
commercial availability of the catalyst make the procedure an attractive alternative to the
existing methods for the synthesis of naphthoxazine-3-one derivatives.
ACKNOWLEDGMENTS
We are thankful to the Islamic Azad University, Tonekabon Branch for the partial support of
this work.
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