Efficient synthesis of novel benzo [f]imidazo[1,2-d][1,4]oxazepine-5(6H)-one derivatives

Efficient synthesis of novel benzo [f]imidazo[1,2-d][1,4]oxazepine-5(6H)-one derivatives Keywords Oxazepine  1,2-Diketones  Ammonium acetate  2-Formyl phenoxy acetic acid  Cyclization Electronic supplementary material The online version of this article (doi:10.1007/s11164-016-2825-z) contains supplementary material, which is available to authorized users. & Heshmatoallah Alinezhad Heshmat@umz.ac.ir Faculty of Chemistry, University of Mazandaran, Babolsr, Iran 123 3284 H. Yavari et al. Introduction Compounds containing a fused seven-membered benzoxazepine ring have been of pivotal interest over the past few years due to their wide range of biological activities and pharmacological properties [1–5]. In particular, 1,4-benzoxazepine derivatives are of pharmaceutical interest because of their activity on the central nervous system as enzyme inhibitors, analgesics, and sedatives, and for their antitumor activity [6–9]. Substituted fused benzoxazepine rings have been identified as PI3-kinase inhibitors for cancer. For instance, 5,6 dihydrobenzo[f]imidazo[1,2- d][1,4]oxazepine scaffolds (Fig. 1) are very promising therapeutics for the treatment of various types of cancers. The synthesis of 2,3,4,5-tetrahydro-1,4-benzoax- azepines often involves the reduction of carbonyl groups as in 5-oxo-2,3,4,5- tetrahydro-1,4-benzoxazepine, or the reduction of a double bond as in 2,3-dihydro- 1,4-bezoxazepine [10]. Alternatively, 2,3,4,5-tetrahydro-1,4-benzoxazepines can be prepared using one of the following benzoxazepine synthetic methods: (1) reaction of 2-aryloxyethy- lamines with 2-formylbenzoic acid to form aminonaphtalides followed by cyclization; (2) rearrangement http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Efficient synthesis of novel benzo [f]imidazo[1,2-d][1,4]oxazepine-5(6H)-one derivatives

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Publisher
Springer Netherlands
Copyright
Copyright © 2016 by Springer Science+Business Media Dordrecht
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-016-2825-z
Publisher site
See Article on Publisher Site

Abstract

Keywords Oxazepine  1,2-Diketones  Ammonium acetate  2-Formyl phenoxy acetic acid  Cyclization Electronic supplementary material The online version of this article (doi:10.1007/s11164-016-2825-z) contains supplementary material, which is available to authorized users. & Heshmatoallah Alinezhad Heshmat@umz.ac.ir Faculty of Chemistry, University of Mazandaran, Babolsr, Iran 123 3284 H. Yavari et al. Introduction Compounds containing a fused seven-membered benzoxazepine ring have been of pivotal interest over the past few years due to their wide range of biological activities and pharmacological properties [1–5]. In particular, 1,4-benzoxazepine derivatives are of pharmaceutical interest because of their activity on the central nervous system as enzyme inhibitors, analgesics, and sedatives, and for their antitumor activity [6–9]. Substituted fused benzoxazepine rings have been identified as PI3-kinase inhibitors for cancer. For instance, 5,6 dihydrobenzo[f]imidazo[1,2- d][1,4]oxazepine scaffolds (Fig. 1) are very promising therapeutics for the treatment of various types of cancers. The synthesis of 2,3,4,5-tetrahydro-1,4-benzoax- azepines often involves the reduction of carbonyl groups as in 5-oxo-2,3,4,5- tetrahydro-1,4-benzoxazepine, or the reduction of a double bond as in 2,3-dihydro- 1,4-bezoxazepine [10]. Alternatively, 2,3,4,5-tetrahydro-1,4-benzoxazepines can be prepared using one of the following benzoxazepine synthetic methods: (1) reaction of 2-aryloxyethy- lamines with 2-formylbenzoic acid to form aminonaphtalides followed by cyclization; (2) rearrangement

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Dec 21, 2016

References

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