Efficient Construction of Tetracyclic 1,2,4‐Triazoline‐Fused Dibenzo[b,f][1,4]oxazepines through KI/TBHP‐Mediated [3+2] Annulation between DBO‐Imines and N‐Tosylhydrazones

The KI/TBHP (tert‐butyl hydroperoxide) promoted [3+2] annulation between dibenzo[b,f][1,4]oxazepine‐imines (DBO‐Imines) and N‐tosylhydrazones under mild conditions has been developed, affording a direct and high atom‐economical preparation for tetracyclic 1,2,4‐triazoline‐fused dibenzo[b,f][1,4]oxaz...

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Published in:European journal of organic chemistry 2022-09, Vol.2022 (35), p.n/a
Main Authors: Wang, Chuan‐Chuan, Wang, Xin‐Lu, Ding, Degang, Ma, Zhi‐Wei, Liu, Zhijing, Chen, Xiao‐Pei, Chen, Ya‐Jing
Format: Article
Language:English
Subjects:
1,2,4-Triazolines
1,2,4-Triazolo-fused
[3+2] Annulation
Dibenzo[b,f][1,4]oxazepine-imines (DBO-Imines)
N-Tosylhydrazones
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Summary:The KI/TBHP (tert‐butyl hydroperoxide) promoted [3+2] annulation between dibenzo[b,f][1,4]oxazepine‐imines (DBO‐Imines) and N‐tosylhydrazones under mild conditions has been developed, affording a direct and high atom‐economical preparation for tetracyclic 1,2,4‐triazoline‐fused dibenzo[b,f][1,4]oxazepines (DBOs) in good to excellent yields. This procedure could tolerate a wide range of functional groups and could also be conveniently conducted on a gram‐scale reaction, even in a one‐pot fashion. The produced 1,2,4‐triazoline‐fused DBOs could be easily converted into biologically interesting 1,2,4‐triazolo‐fused DBOs under the action of NBS (N‐bromosuccinimide). A straightforward protocol for 1,2,4‐triazoline‐fused dibenzo[b,f][1,4]oxazepines is effectively established through KI/TBHP‐promoted [3+2] annulation between dibenzo[b,f][1,4]oxazepine‐imines and N‐tosylhydrazones under mild conditions. The produced 1,2,4‐triazoline‐fused DBOs could be easily converted into biologically interesting 1,2,4‐triazolo‐fused DBOs with excellent yields
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202200888