Abstract
A series of quinoxaline derivatives was synthesized by the reaction
of 3-(ω-bromoacetyl)coumarins with substituted 1,2-diaminobenzenes
in the absence of a catalyst under microwave conditions. Reasonable
yields of the products, environmentally benign and convenient workup
are the advantages of this method.
Key words
quinoxaline - heterocycles - green chemistry - 3-(ω-bromoacetyl)coumarin - microwave irradiation
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26
Typical Procedure
for the Synthesis of Quinoxaline 3a
3-(ω-Bromoacetyl)coumarin 1a (1 mmol) and 1,2-diaminobenzene 2a (1 mmol) were mixed in EtOH (2 mL) and
sealed with a cap containing a septum. The loaded vial was then
placed into the cavity of the microwave reactor and heated at 100 ˚C
for 8 min (as indicated by TLC). After completion of the reaction,
the reaction mixture was then allowed to cool to r.t., resulting
in the precipitation of the solid product. The product was filtered
off and dried. The crude product was subjected to 95% EtOH
for recrystallization to afford the pure product; mp 198.8-199.0 ˚C.
IR (KBr): 3062, 1718, 1610, 1565, 1200, 998, 756 cm-¹ . ¹ H
NMR (400 MHz, CDCl3 ): δ = 7.41
(t, 1 H, J = 15.2Hz), 7.47
(d, 1 H, J = 8.4
Hz), 7.67 (t, 1 H, J = 15.6
Hz), 7.76 (d, 1 H, J = 7.2
Hz), 7.82-7.87 (m, 2 H), 8.17-8.23 (m, 2 H), 8.91
(s, 1 H), 9.86 (s, 1 H). ¹³ C NMR (100
MHz, CDCl3 ): δ = 116.67,
119.36, 124.05, 124.89, 129.14, 129.29, 129.37, 130.31, 130.34,
132.96, 142.12, 142.17, 144.56, 145.34, 147.36, 154.46, 160.10.
ESI-HRMS: m/z calcd for C17 H11 N2 O2 [M + H]+ :
275.0821; found: 275.0339.
