Copper-Catalyzed Synthesis of 2-Arylquinazolinones from 2-Arylindoles with Amines or Ammoniums

Feng, Yadong; Li, Yudong; Cheng, Guolin; Wang, Lianhui; Cui, Xiuling

doi:10.1021/acs.joc.5b00957

Cited by 62 publications

(20 citation statements)

References 47 publications

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“…6‐Bromo‐2‐phenylquinazolin‐4(3 H )‐one (5 ga) : White solid; 87 % yield (262 mg); m.p. 285–286 °C; 1 H NMR (500 MHz, [D 6 ]DMSO): δ =12.71 (br s, 1 H), 8.22 (d, J =2.1 Hz, 1 H), 8.17 (d, J =7.5 Hz, 2 H), 7.98 (dd, J =8.7 Hz and 2.0 Hz, 1 H), 7.69 (d, J =8.7 Hz, 1 H), 7.60 (t, J =7.1 Hz, 1 H), 7.55 ppm (t, J =7.4 Hz, 2 H); 13 C { 1 H} NMR (125 MHz, [D 6 ]DMSO): δ =161.2, 153.0, 147.7, 137.4, 132.5, 131.6, 129.8, 128.6, 128.0, 127.9, 122.6, 118.9 ppm.…”

Section: Methodsmentioning

confidence: 99%

Quinazolinones from o‐Aminobenzonitriles by One‐Pot Sequential Selective Hydration/Condensation/Acceptorless Dehydrogenation Catalyzed by an Iridium Complex

Zhao

Liu

2016

ChemCatChem

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A new strategy for the direct synthesis of quinazolinones from o‐aminobenzonitriles was proposed and accomplished. In the presence of [Cp*IrCl2]2 (Cp*=pentamethylcyclopentadienyl), a variety of desirable products was obtained easily through the one‐pot sequential selective hydration/condensation/acceptorless dehydrogenation. This protocol is highly attractive because it uses readily available starting materials, has a high atom efficiency, good to excellent yields, and minimal consumption of chemicals and energy. Notably, this research exhibited new potential for the development of transition‐metal‐catalyzed one‐pot sequential reactions that involve acceptorless dehydrogenation.

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Section: Methodsmentioning

confidence: 99%

Quinazolinones from o‐Aminobenzonitriles by One‐Pot Sequential Selective Hydration/Condensation/Acceptorless Dehydrogenation Catalyzed by an Iridium Complex

Zhao

Liu

2016

ChemCatChem

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“…O 2 is a very common oxidant that is widely used in various reactions. In 2015, Cui group synthesized quinazolinone derivatives via CuBr‐catalyzed tandem reaction of 2‐arylindoles and amines (Scheme ) . This method was the first example to prepare quinazolinones from easily available materials by sequential Baeyer‐Villiger oxidation expansion under O 2 , hydrolysis, amination, and dehydration/condensation.…”

Section: Additive Effect On the Tandem Reactionmentioning

confidence: 99%

Additive Effects on Copper‐Catalyzed Tandem Reactions

Wu¹,

Ma²,

Xie

2019

Asian J Org Chem

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Introduction of a suitable additive to coppercatalyzed tandem reactions during heterocyclic synthesis is an efficient strategy. This short review mainly describes the results obtained over the period of January 2014 to December 2018 in the area of copper-catalyzed intramolecular tandem reactions to synthesize heterocyclic compounds.Five types of additives that can be used to improve reactivity and selectivity of these tandem reactions were highlighted. Particular attention is paid to demonstrate the importance of additives by comparing results obtained in its absence and presence, and the probable mechanistic role of the additive is discussed based on original articles. . Cu(MeCN) 4 PF 4 -catalyzed reaction of 1,n-enynes and α-carbonyl alkyl bromides. Scheme 33. Cu(OTf) 2 -catalyzed reaction of amino acids and 2-benzoylquinolines. Scheme 34. CuI-catalyzed reaction of o-iodoaniline derivatives S 8 and Ntosylhydrazone. 2 3 4 5 6 7 8

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“…Langer and co-workers [ 36 ] provided a green protocol so that dihydroquinazolinons can be prepared in H 2 O with good yields, whereas quinazolinones can only be obtained by adding oxidant TBHP(tert-butyl hydroperoxide). In the context of green chemistry, water was widely explored as a solvent in various reactions [ 40 , 41 , 42 , 43 ], not only due to its low cost, non-toxicity, easy availability, and eco-benign features, but also because the theoretical and practical advantages of water substantially improved the “on-water” reaction [ 44 , 45 , 46 ]. To date, water has never been used as media to synthesize quinazolinones directly without adding any oxidant.…”

Section: Introductionmentioning

confidence: 99%

“On-Water” Synthesis of Quinazolinones and Dihydroquinazolinones Starting from o-Bromobenzonitrile

Zibin

Zeng

et al. 2018

Molecules

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A versatile and practical “on-water” protocol was newly developed to synthesize quinazolinones using o-bromobenzonitrile as a novel starting material. Studies have found that air as well as water plays an important role in synthesis of quinazolinones. Further investigation indicated that dihydroquinazolinones can be prepared with this protocol under the protection of N2. The protocol can be extended to other substrates and various quinazolinones and dihydroquinazolinones were obtained. o-Bromobenzamide, o-aminobenzonitrile, and o-aminobenzamide were also evaluated as starting materials, and the results further proved the versatility of this protocol, especially towards dihydroquinazolinones.

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Copper-Catalyzed Synthesis of 2-Arylquinazolinones from 2-Arylindoles with Amines or Ammoniums

Cited by 62 publications

References 47 publications

Quinazolinones from o‐Aminobenzonitriles by One‐Pot Sequential Selective Hydration/Condensation/Acceptorless Dehydrogenation Catalyzed by an Iridium Complex

Quinazolinones from o‐Aminobenzonitriles by One‐Pot Sequential Selective Hydration/Condensation/Acceptorless Dehydrogenation Catalyzed by an Iridium Complex

Additive Effects on Copper‐Catalyzed Tandem Reactions

“On-Water” Synthesis of Quinazolinones and Dihydroquinazolinones Starting from o-Bromobenzonitrile

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