Dearomatization of Halonaphthols via an Intermolecular [4＋1] Spiroannulation with in situ Formed Aza-ortho-quinone Methides

Junxiu Liang; Yazhou Liu; Amu Wang; Yanchao Wu; Xiaofeng Ma; Huijing Li

doi:10.6023/cjoc202303029

Dearomatization of Halonaphthols via an Intermolecular [4＋1] Spiroannulation with in situ Formed Aza-ortho-quinone Methides

Junxiu Liang
, Yazhou Liu
, Amu Wang
, Yanchao Wu
, Xiaofeng Ma^*
, Huijing Li^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering, Harbin Institute of Technology
CAS - Chengdu Institute of Biology

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

2 Scopus citations

Abstract

A base promoted dearomatization strategy for [4＋1] spiroannulation of halonaphthols with N-(o-chloromethyl) aryl amides is reported, which is used to efficiently synthesize azaspirocycles. A range of azaspirocycles were obtained in satisfactory to excellent yield with high diastereoselectivity under mild conditions. Variety functional groups including aldehyde and free hydroxyl group, and different N-protecting groups, such as Bz and Ts are compatibility. The transformation of the product and a possible mechanism were also provided.

Translated title of the contribution	基于原位形成的氮杂邻亚甲基苯醌和卤代萘酚的分子间[4＋1]螺环化/去芳香化反应
Original language	English
Pages (from-to)	3888-3899
Number of pages	12
Journal	Chinese Journal of Organic Chemistry
Volume	43
Issue number	11
DOIs	https://doi.org/10.6023/cjoc202303029
State	Published - Nov 2023
Externally published	Yes

Keywords

[4＋1] cycloaddition reaction
azaspirocyclic compound
dearomatization
spiroannulation

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10.6023/cjoc202303029

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title = "Dearomatization of Halonaphthols via an Intermolecular [4＋1] Spiroannulation with in situ Formed Aza-ortho-quinone Methides",

abstract = "A base promoted dearomatization strategy for [4＋1] spiroannulation of halonaphthols with N-(o-chloromethyl) aryl amides is reported, which is used to efficiently synthesize azaspirocycles. A range of azaspirocycles were obtained in satisfactory to excellent yield with high diastereoselectivity under mild conditions. Variety functional groups including aldehyde and free hydroxyl group, and different N-protecting groups, such as Bz and Ts are compatibility. The transformation of the product and a possible mechanism were also provided.",

keywords = "[4＋1] cycloaddition reaction, azaspirocyclic compound, dearomatization, spiroannulation",

author = "Junxiu Liang and Yazhou Liu and Amu Wang and Yanchao Wu and Xiaofeng Ma and Huijing Li",

note = "Publisher Copyright: {\textcopyright} 2023 Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences.",

year = "2023",

month = nov,

doi = "10.6023/cjoc202303029",

language = "英语",

volume = "43",

pages = "3888--3899",

journal = "Chinese Journal of Organic Chemistry",

issn = "0253-2786",

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number = "11",

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TY - JOUR

T1 - Dearomatization of Halonaphthols via an Intermolecular [4＋1] Spiroannulation with in situ Formed Aza-ortho-quinone Methides

AU - Liang, Junxiu

AU - Liu, Yazhou

AU - Wang, Amu

AU - Wu, Yanchao

AU - Ma, Xiaofeng

AU - Li, Huijing

PY - 2023/11

Y1 - 2023/11

N2 - A base promoted dearomatization strategy for [4＋1] spiroannulation of halonaphthols with N-(o-chloromethyl) aryl amides is reported, which is used to efficiently synthesize azaspirocycles. A range of azaspirocycles were obtained in satisfactory to excellent yield with high diastereoselectivity under mild conditions. Variety functional groups including aldehyde and free hydroxyl group, and different N-protecting groups, such as Bz and Ts are compatibility. The transformation of the product and a possible mechanism were also provided.

AB - A base promoted dearomatization strategy for [4＋1] spiroannulation of halonaphthols with N-(o-chloromethyl) aryl amides is reported, which is used to efficiently synthesize azaspirocycles. A range of azaspirocycles were obtained in satisfactory to excellent yield with high diastereoselectivity under mild conditions. Variety functional groups including aldehyde and free hydroxyl group, and different N-protecting groups, such as Bz and Ts are compatibility. The transformation of the product and a possible mechanism were also provided.

KW - [4＋1] cycloaddition reaction

KW - azaspirocyclic compound

KW - dearomatization

KW - spiroannulation

UR - https://www.scopus.com/pages/publications/85181132219

U2 - 10.6023/cjoc202303029

DO - 10.6023/cjoc202303029

M3 - 文章

AN - SCOPUS:85181132219

SN - 0253-2786

VL - 43

SP - 3888

EP - 3899

JO - Chinese Journal of Organic Chemistry

JF - Chinese Journal of Organic Chemistry

IS - 11

ER -

Dearomatization of Halonaphthols via an Intermolecular [4＋1] Spiroannulation with in situ Formed Aza-ortho-quinone Methides

Abstract

Keywords

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