Rhodium(III)-Catalyzed Redox-Neutral [3+3] Annulation of <i>N</i>-nitrosoanilines with Cyclopropenones: A Traceless Approach to Quinolin-4(1<i>H</i>)-One Scaffolds

A traceless approach to quinolin-4(1<i>H</i>)-one scaffolds through Rh(III)-catalyzed redox-neutral [3+3] cyclization of <i>N</i>-nitrosoanilines with cyclopropenones has been achieved. This protocol features short reaction time and atom-economical combination without extra a...

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Main Authors: Lingjun Liu, Jiyuan Li, Wenhao Dai, Feng Gao, Kaixian Chen, Yu Zhou, Hong Liu
Format: Article
Language:English
Published: MDPI AG 2020-01-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/25/2/268
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author Lingjun Liu
Jiyuan Li
Wenhao Dai
Feng Gao
Kaixian Chen
Yu Zhou
Hong Liu
author_facet Lingjun Liu
Jiyuan Li
Wenhao Dai
Feng Gao
Kaixian Chen
Yu Zhou
Hong Liu
author_sort Lingjun Liu
collection DOAJ
description A traceless approach to quinolin-4(1<i>H</i>)-one scaffolds through Rh(III)-catalyzed redox-neutral [3+3] cyclization of <i>N</i>-nitrosoanilines with cyclopropenones has been achieved. This protocol features short reaction time and atom-economical combination without extra additives, which can be further applied in the construction of privileged heterocyclic compounds in pharmaceutical chemistry.
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spelling doaj.art-d970f838c8a24b18a14e186326c8a2c42022-12-21T23:59:58ZengMDPI AGMolecules1420-30492020-01-0125226810.3390/molecules25020268molecules25020268Rhodium(III)-Catalyzed Redox-Neutral [3+3] Annulation of <i>N</i>-nitrosoanilines with Cyclopropenones: A Traceless Approach to Quinolin-4(1<i>H</i>)-One ScaffoldsLingjun Liu0Jiyuan Li1Wenhao Dai2Feng Gao3Kaixian Chen4Yu Zhou5Hong Liu6State Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, ChinaState Key Laboratory of Drug Research and Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, ChinaState Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, ChinaState Key Laboratory of Drug Research and Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, ChinaState Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, ChinaState Key Laboratory of Drug Research and Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, ChinaState Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, ChinaA traceless approach to quinolin-4(1<i>H</i>)-one scaffolds through Rh(III)-catalyzed redox-neutral [3+3] cyclization of <i>N</i>-nitrosoanilines with cyclopropenones has been achieved. This protocol features short reaction time and atom-economical combination without extra additives, which can be further applied in the construction of privileged heterocyclic compounds in pharmaceutical chemistry.https://www.mdpi.com/1420-3049/25/2/268rhodium(iii)redox-neutral[3+3] annulation<i>n</i>-nitrosoanilinecyclopropenonesquinolin-4(1<i>h</i>)-ones
spellingShingle Lingjun Liu
Jiyuan Li
Wenhao Dai
Feng Gao
Kaixian Chen
Yu Zhou
Hong Liu
Rhodium(III)-Catalyzed Redox-Neutral [3+3] Annulation of <i>N</i>-nitrosoanilines with Cyclopropenones: A Traceless Approach to Quinolin-4(1<i>H</i>)-One Scaffolds
Molecules
rhodium(iii)
redox-neutral
[3+3] annulation
<i>n</i>-nitrosoaniline
cyclopropenones
quinolin-4(1<i>h</i>)-ones
title Rhodium(III)-Catalyzed Redox-Neutral [3+3] Annulation of <i>N</i>-nitrosoanilines with Cyclopropenones: A Traceless Approach to Quinolin-4(1<i>H</i>)-One Scaffolds
title_full Rhodium(III)-Catalyzed Redox-Neutral [3+3] Annulation of <i>N</i>-nitrosoanilines with Cyclopropenones: A Traceless Approach to Quinolin-4(1<i>H</i>)-One Scaffolds
title_fullStr Rhodium(III)-Catalyzed Redox-Neutral [3+3] Annulation of <i>N</i>-nitrosoanilines with Cyclopropenones: A Traceless Approach to Quinolin-4(1<i>H</i>)-One Scaffolds
title_full_unstemmed Rhodium(III)-Catalyzed Redox-Neutral [3+3] Annulation of <i>N</i>-nitrosoanilines with Cyclopropenones: A Traceless Approach to Quinolin-4(1<i>H</i>)-One Scaffolds
title_short Rhodium(III)-Catalyzed Redox-Neutral [3+3] Annulation of <i>N</i>-nitrosoanilines with Cyclopropenones: A Traceless Approach to Quinolin-4(1<i>H</i>)-One Scaffolds
title_sort rhodium iii catalyzed redox neutral 3 3 annulation of i n i nitrosoanilines with cyclopropenones a traceless approach to quinolin 4 1 i h i one scaffolds
topic rhodium(iii)
redox-neutral
[3+3] annulation
<i>n</i>-nitrosoaniline
cyclopropenones
quinolin-4(1<i>h</i>)-ones
url https://www.mdpi.com/1420-3049/25/2/268
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