Silver-Mediated [2 + 2 + 1] Cyclization of ortho-Propioloylbenzonitriles with Elemental Selenium: Synthesis of 4H-indeno[1,2-c][1,2]selenazol-4-ones

Nana Fei; Ye Wang; Yingge Gu; Zongkang Wang; Yilin Zhu; Yanzhong Li

doi:10.1021/acs.joc.3c01172

Silver-Mediated [2 + 2 + 1] Cyclization of ortho-Propioloylbenzonitriles with Elemental Selenium: Synthesis of 4H-indeno[1,2-c][1,2]selenazol-4-ones

Nana Fei
, Ye Wang
, Yingge Gu
, Zongkang Wang
, Yilin Zhu
, Yanzhong Li^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

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

4 Scopus citations

Abstract

An efficient silver-mediated [2 + 2 + 1] cyclization protocol of ortho-propioloylbenzonitriles with elemental selenium for the synthesis of 4H-indeno[1,2-c][1,2]selenazol-4-ones has been developed. One C-Se bond, one N-Se bond, and one C-C bond were rapidly constructed in one step. The reaction might proceed via the formation of a highly reactive selenoketene intermediate, followed by intramolecular cyclization.

Original language	English
Pages (from-to)	13042-13048
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	88
Issue number	18
DOIs	https://doi.org/10.1021/acs.joc.3c01172
State	Published - 15 Sep 2023

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title = "Silver-Mediated [2 + 2 + 1] Cyclization of ortho-Propioloylbenzonitriles with Elemental Selenium: Synthesis of 4H-indeno[1,2-c][1,2]selenazol-4-ones",

abstract = "An efficient silver-mediated [2 + 2 + 1] cyclization protocol of ortho-propioloylbenzonitriles with elemental selenium for the synthesis of 4H-indeno[1,2-c][1,2]selenazol-4-ones has been developed. One C-Se bond, one N-Se bond, and one C-C bond were rapidly constructed in one step. The reaction might proceed via the formation of a highly reactive selenoketene intermediate, followed by intramolecular cyclization.",

author = "Nana Fei and Ye Wang and Yingge Gu and Zongkang Wang and Yilin Zhu and Yanzhong Li",

note = "Publisher Copyright: {\textcopyright} 2023 American Chemical Society.",

year = "2023",

month = sep,

day = "15",

doi = "10.1021/acs.joc.3c01172",

language = "英语",

volume = "88",

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TY - JOUR

T1 - Silver-Mediated [2 + 2 + 1] Cyclization of ortho-Propioloylbenzonitriles with Elemental Selenium

T2 - Synthesis of 4H-indeno[1,2-c][1,2]selenazol-4-ones

AU - Fei, Nana

AU - Wang, Ye

AU - Gu, Yingge

AU - Wang, Zongkang

AU - Zhu, Yilin

AU - Li, Yanzhong

PY - 2023/9/15

Y1 - 2023/9/15

N2 - An efficient silver-mediated [2 + 2 + 1] cyclization protocol of ortho-propioloylbenzonitriles with elemental selenium for the synthesis of 4H-indeno[1,2-c][1,2]selenazol-4-ones has been developed. One C-Se bond, one N-Se bond, and one C-C bond were rapidly constructed in one step. The reaction might proceed via the formation of a highly reactive selenoketene intermediate, followed by intramolecular cyclization.

AB - An efficient silver-mediated [2 + 2 + 1] cyclization protocol of ortho-propioloylbenzonitriles with elemental selenium for the synthesis of 4H-indeno[1,2-c][1,2]selenazol-4-ones has been developed. One C-Se bond, one N-Se bond, and one C-C bond were rapidly constructed in one step. The reaction might proceed via the formation of a highly reactive selenoketene intermediate, followed by intramolecular cyclization.

UR - https://www.scopus.com/pages/publications/85171563884

U2 - 10.1021/acs.joc.3c01172

DO - 10.1021/acs.joc.3c01172

M3 - 文章

AN - SCOPUS:85171563884

SN - 0022-3263

VL - 88

SP - 13042

EP - 13048

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 18

ER -

Silver-Mediated [2 + 2 + 1] Cyclization of ortho-Propioloylbenzonitriles with Elemental Selenium: Synthesis of 4H-indeno[1,2-c][1,2]selenazol-4-ones

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