Vinyl azide as a synthon for DNA-compatible divergent transformations into N-heterocycles†
Jie
Sun, 
‡a
Qigui
Nie,
‡a
Xianfu
Fang,
a
Zhiwei
He,
a
Gong
Zhang,
ab
Yangfeng
Li
*ab
and
Yizhou
Li
*abcd
‡a
Qigui
Nie,
‡a
Xianfu
Fang,
a
Zhiwei
He,
a
Gong
Zhang,
ab
Yangfeng
Li
*ab
and
Yizhou
Li
*abcd
Abstract
Inspired by diversity-oriented synthesis, we have developed a series of DNA-compatible transformations utilizing on-DNA vinyl azide as a synthon to forge divergent N-heterocyclic scaffolds. Polysubstituted imidazoles and isoquinolines were efficiently obtained with moderate-to-excellent conversions. Besides, the “one-pot” strategy to prepare in-house on-DNA vinyl azides afforded synthons readily. Results from substrate scope exploration and enzymatic ligation further demonstrate the feasibility of these N-heterocycle syntheses in DNA-encoded chemical library construction.
- This article is part of the themed collection: Synthetic methodology in OBC
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