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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 30, Number 6
BKCSDE 30(6)
June 20, 2009 

Solid-phase Synthesis of 7-Aryl-benzo[b][1,4]oxazin-3(4H)-one Derivatives on a BOMBA Resin Utilizing the Smiles Rearrangement
Ji Min Lee, Eun Ae Yu, Joo Yeon Park, In Ae Ryu, Dong Soo Shin, Young Dae Gong*
Solid-phase synthesis, Benzo[b][1,4]oxazin, Smiles rearrangement, Microwave irradiation, BOMBA resin.
A general method has been developed for the solid phase synthesis of drug-like 7-aryl-benzo[b][1,4]oxazin-3(4H)-one derivatives 6. The method relies on a novel, microwave irradiation promoted cyclization reaction of the BOMBA resin bound, N-substituted-α-(2-chloro-4-bromophenoxy)acetamide 3 that takes place via a Smiles rearrangement. The 7-bromobenzo[1,4]oxazine 4, produced in this process is converted to 7-aryloxazin analogs 5 by utilizing Suzuki coupling with various substituted arylboronic acids. Finally, the target 7-aryl-benzo[b][1,4]oxazin-3(4H)-ones 6 are liberated from the resin by treatment with 5% TFA. The progress of the reactions involved in this preparative route can be monitored by using ATR-FTIR spectroscopy on a single bead. The target compounds, obtained by using this five-step sequence, are produced in high yields and purities.
1325 - 1330
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