Microwave‐assisted Solid‐phase Synthesis of N‐substituted‐2‐aminobenzo[d][1,3] Thiazine Derivatives from a BOMBA Resin

An efficient solid‐phase methodology has been developed for the synthesis of N‐acyl and N‐sulfonyl substituted 2‐aminobenzo[d][1,3]thiazine derivatives. The key step in this methodology is the preparation of backbone amide linker‐bound 2‐aminobenzo[d][1,3]thiazine resin through cyclization reaction...

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Bibliographic Details
Published in:Bulletin of the Korean Chemical Society 2017, 38(3), , pp.334-341
Main Authors: Jun, Hee‐Goo, Kim, Eun‐Mi, Yoon, Hyo‐Jeong, Gong, Young‐Dae
Format: Article
Language:English
Subjects:
Benzo[d][1,3]thiazine
BOMBA resin
Heterocycles
Solid‐phase parallel synthesis
화학
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Summary:An efficient solid‐phase methodology has been developed for the synthesis of N‐acyl and N‐sulfonyl substituted 2‐aminobenzo[d][1,3]thiazine derivatives. The key step in this methodology is the preparation of backbone amide linker‐bound 2‐aminobenzo[d][1,3]thiazine resin through cyclization reaction between isothiocyanates and BOMBA resin under microwave irradiation. This 2‐aminobenzo[d][1,3]thiazine core skeleton resin undergoes substitution reactions with various electrophiles, such as acid halides and sulfonyl halides, to generate N‐acyl and N‐sulfonyl substituted 2‐aminobenzo[d][1,3]thiazine resins, respectively. Finally, N‐acyl and N‐sulfonyl‐substituted 2‐aminobenzo[d][1,3]thiazine derivatives are prepared in good yields and purities by cleavage of the respective resins under trifluoroacetic acid (TFA) in dichloromethane (DCM).
ISSN:1229-5949
0253-2964
1229-5949
DOI:10.1002/bkcs.11088