One-step synthesis of benzo[g]phthalazines and naphtho[2,3-g]phthalazines from benzo- or naphtho-oxabicyclic alkene

An efficient protocol for one-step synthesis of oxadisilole-fused benzo[g]phthalazines and naphtho[2,3-g]phthalazines by the Diels-Alder reactions and denitrogenation/deoxygenation aromatization reactions of benzo- or naphtho-oxabicyclic alkene with 3,6-diaryl-1,2,4,5-tetrazines in THF at room tempe...

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Bibliographic Details
Published inTetrahedron Vol. 73; no. 48; pp. 6742 - 6746
Main Authors Kong, Kundi, Zhang, Jie, Zhao, Peng, Lu, Huali, Chen, Zhijun, Cao, Weiguo, Chen, Jie, Chen, Yali
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 30.11.2017
Elsevier
Subjects
Benzo-oxabicyclic alkene
Benzo[g]phthalazines
Chemistry
Chemistry, Organic
Naphtho-oxabicyclic alkene
Naphtho[2,3-g]phthalazines
Physical Sciences
Science & Technology
Naphtho-oxabicyclic alkene
Benzo[g]phthalazines
Benzo-oxabicyclic alkene
Naphtho[2,3-g]phthalazines
CYCLOADDITION
COMPLEXES
ISOBENZOFURANS
OXADISILOLE
DERIVATIVES
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Summary:An efficient protocol for one-step synthesis of oxadisilole-fused benzo[g]phthalazines and naphtho[2,3-g]phthalazines by the Diels-Alder reactions and denitrogenation/deoxygenation aromatization reactions of benzo- or naphtho-oxabicyclic alkene with 3,6-diaryl-1,2,4,5-tetrazines in THF at room temperature for 3 h. The photophysical, redox, and thermal properties of these compounds have been determined. The proposed mechanism was also studied. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2017.10.028