Synthesis of Pyrano[2,3- b ]indol-4-ones Fused with Medium-Sized Rings: A Base-Induced C-C σ-Bond Insertion and Subsequent i 2 -Mediated 1,2-Acyl Migration/Cyclization Reaction

Yan Wang; Zongkang Wang; Nana Fei; Peng He; Lingkai Kong; Yanzhong Li

doi:10.1055/a-2560-8133

Synthesis of Pyrano[2,3- b ]indol-4-ones Fused with Medium-Sized Rings: A Base-Induced C-C σ-Bond Insertion and Subsequent i ₂ -Mediated 1,2-Acyl Migration/Cyclization Reaction

Yan Wang
, Zongkang Wang
, Nana Fei
, Peng He
, Lingkai Kong^*
, Yanzhong Li

^*此作品的通讯作者

化学与分子工程学院

科研成果: 期刊稿件 › 文章 › 同行评审

摘要

A novel tandem reaction starting from alkynones and cyclic ketones has been developed to efficiently synthesize pyranoindolones fused with a medium-sized ring. This process involves a base-induced C-C σ-bond cleavage reaction of cyclic ketone and subsequent I ₂ -mediated 1,2-acyl migration/cyclization reaction. Transition-metal-free and easily accessible starting materials make this 1,2-acyl migration/cyclization methodology attractive.

源语言	英语
页（从-至）	1508-1513
页数	6
期刊	Synlett
卷	36
期	11
DOI	https://doi.org/10.1055/a-2560-8133
出版状态	已出版 - 10 6月 2025

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10.1055/a-2560-8133

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@article{be848892c8a1489aa8d9579fd3944fbc,

title = "Synthesis of Pyrano[2,3- b ]indol-4-ones Fused with Medium-Sized Rings: A Base-Induced C-C σ-Bond Insertion and Subsequent i 2 -Mediated 1,2-Acyl Migration/Cyclization Reaction",

abstract = "A novel tandem reaction starting from alkynones and cyclic ketones has been developed to efficiently synthesize pyranoindolones fused with a medium-sized ring. This process involves a base-induced C-C σ-bond cleavage reaction of cyclic ketone and subsequent I 2 -mediated 1,2-acyl migration/cyclization reaction. Transition-metal-free and easily accessible starting materials make this 1,2-acyl migration/cyclization methodology attractive.",

keywords = "1,2-acyl migration/cyclization, C-C σ-bond cleavage, mild reaction conditions, one-pot synthesis, transition-metal-free",

author = "Yan Wang and Zongkang Wang and Nana Fei and Peng He and Lingkai Kong and Yanzhong Li",

year = "2025",

month = jun,

day = "10",

doi = "10.1055/a-2560-8133",

language = "英语",

volume = "36",

pages = "1508--1513",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "11",

}

TY - JOUR

T1 - Synthesis of Pyrano[2,3- b ]indol-4-ones Fused with Medium-Sized Rings

T2 - A Base-Induced C-C σ-Bond Insertion and Subsequent i 2 -Mediated 1,2-Acyl Migration/Cyclization Reaction

AU - Wang, Yan

AU - Wang, Zongkang

AU - Fei, Nana

AU - He, Peng

AU - Kong, Lingkai

AU - Li, Yanzhong

PY - 2025/6/10

Y1 - 2025/6/10

N2 - A novel tandem reaction starting from alkynones and cyclic ketones has been developed to efficiently synthesize pyranoindolones fused with a medium-sized ring. This process involves a base-induced C-C σ-bond cleavage reaction of cyclic ketone and subsequent I 2 -mediated 1,2-acyl migration/cyclization reaction. Transition-metal-free and easily accessible starting materials make this 1,2-acyl migration/cyclization methodology attractive.

AB - A novel tandem reaction starting from alkynones and cyclic ketones has been developed to efficiently synthesize pyranoindolones fused with a medium-sized ring. This process involves a base-induced C-C σ-bond cleavage reaction of cyclic ketone and subsequent I 2 -mediated 1,2-acyl migration/cyclization reaction. Transition-metal-free and easily accessible starting materials make this 1,2-acyl migration/cyclization methodology attractive.

KW - 1,2-acyl migration/cyclization

KW - C-C σ-bond cleavage

KW - mild reaction conditions

KW - one-pot synthesis

KW - transition-metal-free

UR - https://www.scopus.com/pages/publications/105003264859

U2 - 10.1055/a-2560-8133

DO - 10.1055/a-2560-8133

M3 - 文章

AN - SCOPUS:105003264859

SN - 0936-5214

VL - 36

SP - 1508

EP - 1513

JO - Synlett

JF - Synlett

IS - 11

ER -

Synthesis of Pyrano[2,3- b ]indol-4-ones Fused with Medium-Sized Rings: A Base-Induced C-C σ-Bond Insertion and Subsequent i 2 -Mediated 1,2-Acyl Migration/Cyclization Reaction

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Synthesis of Pyrano[2,3- b ]indol-4-ones Fused with Medium-Sized Rings: A Base-Induced C-C σ-Bond Insertion and Subsequent i ₂ -Mediated 1,2-Acyl Migration/Cyclization Reaction