Synthesis of Polycyclic Benzo[b]indolo[3,2,1-de]acridines via Sequential Allenylation, Diels-Alder Cyclization, and Hydrogen Migration Reaction

Yulei Zhao; Yang Yuan; Xiaoyu Wang; Yanzhong Li

doi:10.1021/acs.joc.7b01614

Synthesis of Polycyclic Benzo[b]indolo[3,2,1-de]acridines via Sequential Allenylation, Diels-Alder Cyclization, and Hydrogen Migration Reaction

Yulei Zhao
, Yang Yuan
, Xiaoyu Wang
, 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

8 Scopus citations

Abstract

A novel methodology for stereoselective synthesis of benzo[b]indolo[3,2,1-de]acridines through the tandem reaction of propargylic compounds with organoboron is described, and only one diastereoisomer was obtained. The sequential procedure was triggered by Pd(0)-catalyzed allenylation of propargyl carbonate. Then, Diels-Alder cyclization and hydrogen migration processes proceeded successively to furnish the polycyclic target molecules. Control reactions suggested the base (Cs₂CO₃) was indispensable for the hydrogen migration.

Original language	English
Pages (from-to)	11198-11205
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	82
Issue number	20
DOIs	https://doi.org/10.1021/acs.joc.7b01614
State	Published - 20 Oct 2017

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title = "Synthesis of Polycyclic Benzo[b]indolo[3,2,1-de]acridines via Sequential Allenylation, Diels-Alder Cyclization, and Hydrogen Migration Reaction",

abstract = "A novel methodology for stereoselective synthesis of benzo[b]indolo[3,2,1-de]acridines through the tandem reaction of propargylic compounds with organoboron is described, and only one diastereoisomer was obtained. The sequential procedure was triggered by Pd(0)-catalyzed allenylation of propargyl carbonate. Then, Diels-Alder cyclization and hydrogen migration processes proceeded successively to furnish the polycyclic target molecules. Control reactions suggested the base (Cs2CO3) was indispensable for the hydrogen migration.",

author = "Yulei Zhao and Yang Yuan and Xiaoyu Wang and Yanzhong Li",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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T1 - Synthesis of Polycyclic Benzo[b]indolo[3,2,1-de]acridines via Sequential Allenylation, Diels-Alder Cyclization, and Hydrogen Migration Reaction

AU - Zhao, Yulei

AU - Yuan, Yang

AU - Wang, Xiaoyu

AU - Li, Yanzhong

PY - 2017/10/20

Y1 - 2017/10/20

N2 - A novel methodology for stereoselective synthesis of benzo[b]indolo[3,2,1-de]acridines through the tandem reaction of propargylic compounds with organoboron is described, and only one diastereoisomer was obtained. The sequential procedure was triggered by Pd(0)-catalyzed allenylation of propargyl carbonate. Then, Diels-Alder cyclization and hydrogen migration processes proceeded successively to furnish the polycyclic target molecules. Control reactions suggested the base (Cs2CO3) was indispensable for the hydrogen migration.

AB - A novel methodology for stereoselective synthesis of benzo[b]indolo[3,2,1-de]acridines through the tandem reaction of propargylic compounds with organoboron is described, and only one diastereoisomer was obtained. The sequential procedure was triggered by Pd(0)-catalyzed allenylation of propargyl carbonate. Then, Diels-Alder cyclization and hydrogen migration processes proceeded successively to furnish the polycyclic target molecules. Control reactions suggested the base (Cs2CO3) was indispensable for the hydrogen migration.

UR - https://www.scopus.com/pages/publications/85031919629

U2 - 10.1021/acs.joc.7b01614

DO - 10.1021/acs.joc.7b01614

M3 - 文章

AN - SCOPUS:85031919629

SN - 0022-3263

VL - 82

SP - 11198

EP - 11205

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 20

ER -

Synthesis of Polycyclic Benzo[b]indolo[3,2,1-de]acridines via Sequential Allenylation, Diels-Alder Cyclization, and Hydrogen Migration Reaction

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