Radical Haloazidation of 1,5-Enenitriles for Making N-Haloimines and Sequential Triazolation to Form Tricyclics

Xiaoming Ma; Mifei Yu; Zijie Gao; Jia Yin Wang; Hang Dong Zuo; Sai Zhang; Shenghu Yan; Yue Zhang; Wei Zhang

doi:10.1021/acs.orglett.6c00773

Radical Haloazidation of 1,5-Enenitriles for Making N-Haloimines and Sequential Triazolation to Form Tricyclics

Xiaoming Ma
, Mifei Yu
, Zijie Gao
, Jia Yin Wang
, Hang Dong Zuo
, Sai Zhang
, Shenghu Yan
, Yue Zhang
, Wei Zhang

Chemistry

Changzhou University

Research output: Contribution to journal › Letter › peer-review

Abstract

A new method for making N-haloimines by Mn-catalyzed radical haloazidation of 1,5-enenitriles with TMSN₃ and N-halosuccinimides is introduced. The resulting azido N-haloimines are used for diannulation with alkynes to form triazole-fused heterocycles via a cascade CuAAC with alkynes and intramolecular electrophilic aromatic substitution (EAS).

Original language	English
Pages (from-to)	4748-4753
Number of pages	6
Journal	Organic Letters
Volume	28
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.6c00773
State	Published - Apr 17 2026

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.6c00773

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title = "Radical Haloazidation of 1,5-Enenitriles for Making N-Haloimines and Sequential Triazolation to Form Tricyclics",

abstract = "A new method for making N-haloimines by Mn-catalyzed radical haloazidation of 1,5-enenitriles with TMSN3 and N-halosuccinimides is introduced. The resulting azido N-haloimines are used for diannulation with alkynes to form triazole-fused heterocycles via a cascade CuAAC with alkynes and intramolecular electrophilic aromatic substitution (EAS).",

author = "Xiaoming Ma and Mifei Yu and Zijie Gao and Wang, \{Jia Yin\} and Zuo, \{Hang Dong\} and Sai Zhang and Shenghu Yan and Yue Zhang and Wei Zhang",

note = "Publisher Copyright: {\textcopyright} 2026 The Authors. Published by American Chemical Society",

year = "2026",

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day = "17",

doi = "10.1021/acs.orglett.6c00773",

language = "English",

volume = "28",

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journal = "Organic Letters",

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TY - JOUR

T1 - Radical Haloazidation of 1,5-Enenitriles for Making N-Haloimines and Sequential Triazolation to Form Tricyclics

AU - Ma, Xiaoming

AU - Yu, Mifei

AU - Gao, Zijie

AU - Wang, Jia Yin

AU - Zuo, Hang Dong

AU - Zhang, Sai

AU - Yan, Shenghu

AU - Zhang, Yue

AU - Zhang, Wei

PY - 2026/4/17

Y1 - 2026/4/17

N2 - A new method for making N-haloimines by Mn-catalyzed radical haloazidation of 1,5-enenitriles with TMSN3 and N-halosuccinimides is introduced. The resulting azido N-haloimines are used for diannulation with alkynes to form triazole-fused heterocycles via a cascade CuAAC with alkynes and intramolecular electrophilic aromatic substitution (EAS).

AB - A new method for making N-haloimines by Mn-catalyzed radical haloazidation of 1,5-enenitriles with TMSN3 and N-halosuccinimides is introduced. The resulting azido N-haloimines are used for diannulation with alkynes to form triazole-fused heterocycles via a cascade CuAAC with alkynes and intramolecular electrophilic aromatic substitution (EAS).

UR - https://www.scopus.com/pages/publications/105035862457

UR - https://www.scopus.com/pages/publications/105035862457#tab=citedBy

U2 - 10.1021/acs.orglett.6c00773

DO - 10.1021/acs.orglett.6c00773

M3 - Letter

C2 - 41934400

AN - SCOPUS:105035862457

SN - 1523-7060

VL - 28

SP - 4748

EP - 4753

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Radical Haloazidation of 1,5-Enenitriles for Making N-Haloimines and Sequential Triazolation to Form Tricyclics

Abstract

ASJC Scopus Subject Areas

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