Concise Synthesis of Thiazolo[4,5‐b]indoles via Ring Switch/Cyclization Sequences

The unexpected reactions of indoline hemiaminals affords 2,5‐diaryl‐4‐hydroxythiazolines through a thioamidation/ring switch sequence. The key to success of this transformation is to use a thioamide as a thiazoline precursor under transient tautomeric control. This transformation features mild react...

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Bibliographic Details
Published in:European journal of organic chemistry 2024-01, Vol.27 (4), p.n/a
Main Authors: Yamada, Koji, Tsubogo, Tetsu, Kanazawa, Hikaru, Ishizuka, Sayaka, Ohyama, Koutaro, Kaida, Masaki, Abe, Takumi
Format: Article
Language:English
Subjects:
hemiaminals
indoles
ring-switch
thiazolo[4.5-b]indoles
thioamides
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Summary:The unexpected reactions of indoline hemiaminals affords 2,5‐diaryl‐4‐hydroxythiazolines through a thioamidation/ring switch sequence. The key to success of this transformation is to use a thioamide as a thiazoline precursor under transient tautomeric control. This transformation features mild reaction conditions and good yields with broad functional group tolerance (17 examples, up to 99 % yield). Further transformations of the thiazolines provide a direct entry to dihydrothiazolo[4,5‐b]indoles and thiazolo[4,5‐b]indoles. Open and shut!!: Unprecedented modular synthesis of thiazolo[4.5‐b]indoles was accomplished by a unique ring switch/cyclization sequences of hemiaminals.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202301130