Issue 38, 2013
From the journal:

Organic & Biomolecular Chemistry

A convenient method to construct (Z)-oxazines via 6-exo-dig iodocyclization and synthesis of indolin-3-one†

Jaya Kishore Vandavasi,‡a   Kung-Kai Kuo,‡b   Wan-Ping Hu,c   Ho-Chanu Shen,a   Wei-Sheng Loa  and  Jeh-Jeng Wang*a  

* Corresponding authors

a Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung, Taiwan
E-mail: jjwang@kmu.edu.tw

b Department of Surgery, School of Medicine, Kaohsiung Medical University, Kaohsiung, Taiwan

c Department of Biotechnology, Kaohsiung Medical University, Kaohsiung, Taiwan

Abstract

An efficient regio-, stereo- and chemo-specific synthesis of 1,3-benzoxazines via 6-exo-dig cyclization to afford the Z-isomer is reported. The structure and connectivity were confirmed unambiguously on the basis of 1H NMR, NOESY, and ORTEP. Furthermore, DFT studies revealed that the Z-isomer was more stable than the E-isomer. Iodine substituted 1,3-benzoxazines were very useful precursors for cross coupling reactions. Suzuki reaction was carried out successfully and the resulting product was transformed to 1-(4-nitrobenzoyl)-2,2-diphenylindolin-3-one in the presence of a Lewis acid.

Graphical abstract: A convenient method to construct (Z)-oxazines via 6-exo-dig iodocyclization and synthesis of indolin-3-one

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Article information

DOI
https://doi.org/10.1039/C3OB41272E
Article type
Paper
Submitted
20 Jun 2013
Accepted
26 Jul 2013
First published
29 Jul 2013

Org. Biomol. Chem., 2013,11, 6520-6525

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A convenient method to construct (Z)-oxazines via 6-exo-dig iodocyclization and synthesis of indolin-3-one

J. K. Vandavasi, K. Kuo, W. Hu, H. Shen, W. Lo and J. Wang, Org. Biomol. Chem., 2013, 11, 6520 DOI: 10.1039/C3OB41272E

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