Synthesis of 3′-allylindoline spirobenzopyrans derived from 3-allyl-3H-indoles

[Display omitted] In this study, 8 new spirobenzopyrans were synthesized. A novel, three-step, facile route for the synthesis of 3′-allylindoline spirobenzopyrans via 3-allyl-3H-indoles was developed. The newly synthesized spirobenzopyrans were evaluated for their photochromic properties. The presen...

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Bibliographic Details
Published in:Tetrahedron letters 2014-11, Vol.55 (47), p.6427-6431
Main Authors: Kagawa, Natsuko, Takabatake, Hiroki, Masuda, Yoshitake
Format: Article
Language:English
Subjects:
Allylation
Chains
Indole
Methodology
Palladium catalyst
Photochromism
Spirobenzopyran
Spiropyran
Steric effects
Synthesis (chemistry)
Tetrahedrons
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Summary:[Display omitted] In this study, 8 new spirobenzopyrans were synthesized. A novel, three-step, facile route for the synthesis of 3′-allylindoline spirobenzopyrans via 3-allyl-3H-indoles was developed. The newly synthesized spirobenzopyrans were evaluated for their photochromic properties. The presence of an allyl moiety at the 3′ position did not disturb the photochromic response. The steric effects of the diallyl groups at the 3′ position affected the interconversion between colored and colorless forms. Therefore, the allyl chain in 3′-allylindoline spirobenzopyrans can be utilized to attach these compounds to a molecular matrix. Consequently, this synthetic methodology could be readily applied to the creation of new photo-switchable materials.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.09.121