- Carbocatalytic Cascade Synthesis of Polysubstituted Quinolines from Aldehydes and 2-Vinyl Anilines
-
Oxidized active carbon (oAC) catalyses the formation of polysubstituted quinolines from o-vinyl anilines and aldehydes. The reaction proceeds in a cascade manner through condensation, electrocyclization and dehydrogenation, and gives access to a wide range of quinolines with alkyl and/or aryl substituents as demonstrated with 40 examples. The metal-free catalytic procedure allows a heterogeneous protocol for the synthesis of various polysubstituted quinolines. The mechanistic studies imply that both the acid and quinoidic groups in oAC are integral for the catalytic manifold. (Figure presented.).
- Bulatov, Evgeny,Helaja, Juho,Hu, Tao,Lenarda, Anna,M?kel?, Mikko K.,Malinen, Kiia,Melchionna, Michele,Nieger, Martin,Talvitie, Juulia,Wirtanen, Tom
-
supporting information
p. 3775 - 3782
(2021/07/20)
-
- PEG-400 as a carbon synthon: Highly selective synthesis of quinolines and methylquinolines under metal-free conditions
-
A metal-free, peroxide-free, and efficient procedure for the highly selective synthesis of quinolines and methylquinolines was reported. The main feature of this method was that the same substrate can produce quinolines and methylquinolines, respectively, under different reaction conditions. PEG-400 was used as both a reactant and solvent in this reaction. The utility of the designed procedure was also demonstrated by the derivatization of the products to bioactive compounds. This journal is
- Ding, Chengcheng,Feng, Kaili,Li, Shichen,Ma, Chen
-
supporting information
p. 5542 - 5548
(2021/08/16)
-
- Synthesis of 1-Amino-2,2,2-trifluoroalkylphosphonates from Alkene-Tethered Trifluoroacetimidoyl Chlorides
-
The reaction of alkene-tethered trifluoroacetimidoyl chlorides with trialkyl phosphites furnishes 1-amino-2,2,2-trifluoroalkylphosphonates. The products were generated in moderate to good yields, and the scalability of this process was showcased. Partial hydrolysis of the phosphonate moiety was achieved. The cyclization is proposed to occur via formation of an imidoyl phosphonate intermediate that becomes susceptible to nucleophilic attack at nitrogen through the strong electron-withdrawing groups at the imidoyl carbon.
- Rodríguez, José F.,Zhang, Anji,Arora, Ramon,Lautens, Mark
-
supporting information
p. 7540 - 7544
(2021/10/12)
-
- Photocatalyzed Intramolecular [2+2] Cycloaddition of N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides
-
N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides are converted into natural product inspired scaffolds via iridium photocatalyzed intramolecular [2+2] photocycloaddition. The protocol has a broad substrate scope, whilst operating under mild reaction conditions. Tethering four components forming a trisubstituted cyclobutane core builds rapidly high molecular complexity. Our approach allows the design and synthesis of a variety of tetrahydrocyclobuta[c]quinolin-3(1H)-ones, in yields ranging between 20–99 %, and with excellent regio- and diastereoselectivity. Moreover, it was demonstrated that the intramolecular [2+2]-cycloaddition of 1,7-enynes—after fragmentation of the cyclobutane ring—leads to enyne-metathesis-like products.
- de Souza, Wanderson C.,Matsuo, Bianca T.,Matos, Priscilla M.,Correia, José Tiago M.,Santos, Marilia S.,K?nig, Burkhard,Paix?o, Marcio W.
-
supporting information
p. 3722 - 3728
(2021/02/03)
-
- Ir(iii)-Catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling for the synthesis of N-H indoles
-
Herein, an iridium(iii)-catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling of unprotected 2-alkenyl anilines is described. The developed method allows the synthesis of a variety of 3-substituted N-H indole scaffolds under undivided electrolytic conditions. Mechanistic studies suggest that the reaction proceeds through the electro-oxidation induced reductive elimination pathway.
- Chang, Sukbok,Kim, Dongwook,Kim, Youyoung
-
p. 12309 - 12312
(2021/12/07)
-
- Palladium-Catalyzed Carbamoyl-Carbamoylation/ Carboxylation/Thioesterification of Alkene-Tethered Carbamoyl Chlorides Using Mo(CO)6 as the Carbonyl Source
-
We reported a palladium-catalyzed carbamoyl-carbamoylation/carboxylation/thioesterification of alkene-tethered carbamoyl chlorides using Mo(CO)6 as the carbonyl source. The reactions were typically performed with good functional group compatibility and tolerated different nucleophiles (amines, alcohols, phenols, thiols and water), which provided a new access to amidated/esterificated/thioesterificated/carboxylated oxindoles or lactams bearing an all-carbon quaternary stereocenter under CO gas-free conditions. Furthermore, natural product mutation and divergent late-stage derivatization are the important practical features.
- Chen, Chen,Ding, Jie,Huang, Yujie,Liu, Liying,Zhu, Bolin
-
supporting information
(2022/01/04)
-
- Palladium(ii)-catalyzed vinylic geminal double C-H activation and alkyne annulation reaction: Synthesis of pentafulvenes
-
The first transition-metal-catalyzed vinylic geminal double C(sp2)-H activation and di-substituted alkyne annulation reaction is reported. This palladium(ii)-catalyzed, amide directed reaction of vinylic compounds with di-substituted alkynes offers an efficient synthetic path to pentafulvenes, which are very important compounds because of their bioactivity and interesting optical properties. A FeCl3-mediated transformation of pentafulvenes to fluorescent cyclopenta[b]quinolines is also developed.
- Phukon, Jyotshna,Gogoi, Sanjib
-
supporting information
p. 1133 - 1136
(2020/02/04)
-
- Mn(III)-Mediated Regioselective 6-endo-trig Radical Cyclization of o-Vinylaryl Isocyanides to Access 2-Functionalized Quinolines
-
A Mn(III)-mediated radical cyclization reaction of o-vinylaryl isocyanides and arylboronic acids or diphenylphosphine oxides to access various 2-functionalized quinolines under mild conditions was developed. With the introduction of radical stabilizing substituents (e. g. aryl and methyl group) on vinyl group, this reaction provides a regiospecific 6-endo-trig radical cyclization of o-vinylaryl isocyanides, giving a number of structurally unique and biologically potential 2-functionalized quinoline derivatives.
- Liu, Yan,Li, Shi-Jun,Chen, Xiao-Lan,Fan, Lu-Lu,Li, Xiao-Yun,Zhu, Shan-Shan,Qu, Ling-Bo,Yu, Bing
-
supporting information
p. 688 - 694
(2020/01/02)
-
- Iodine-Promoted Synthesis of 4-Aryl-2-(arylsulfonyl)quinolones by Desulfurative C-S Cross-Coupling Reaction of Quinoline-2-thiones with Sodium Sulfinates
-
An iodine-induced sulfonylation of quinoline-2-thiones with sodium arenesulfinates as sulfur sources for the synthesis of 4-aryl-2-(arylsulfonyl)quinoline derivatives is described. The 4-aryl-2-(arylsulfonyl)quinoline derivatives can be obtained in a moderate to good yields. This C-S bond cleavage and C-S cross-coupling proceeds in the absence of a metal under inexpensive and nontoxic conditions and it displays a broad substrate scope.
- Yang, Guo-Chao,Wang, Xi-Chun,Quan, Zheng-Jun
-
supporting information
p. 1527 - 1531
(2020/08/24)
-
- Palladium-Catalyzed/Copper-Mediated Desulfurization and Aryl- ation of Quinoline-2-(1 H)-thione for Rapid Access to Quinoline Derivatives
-
An efficient method for carbon-carbon bond formation is described. The process employs the palladium-catalyzed and copper-mediated cross-coupling of quinoline-2-(1 H)-thiones with arylboronic acids or alkynes through C-S bond cleavage without an inert atm
- Guo, Fu-Hu,Lu, Hai-Long,Quan, Zheng-Jun,Wang, Tong-Lin,Wang, Xi-Cun
-
supporting information
p. 893 - 900
(2020/03/13)
-
- Palladium-Catalyzed Phosphoryl-Carbamoylation of Alkenes: Construction of Nonbenzylic C(sp3)?P(O)R2 Bonds via C(sp3)?Pd(II)?P(O)R2 Reductive Elimination
-
We report the first example of palladium-catalyzed phosphoryl-carbamoylation of alkene-tethered carbamoyl chlorides with P(O)H compounds. Both H-phosphinates and secondary phosphine oxides are compatible with this reaction. DPE-Phos was used as ligand to facilitate nonbenzylic C(sp3)?P bonds formations via C(sp3)?Pd(II)?P reductive elimination. By using this protocol, a range of phosphorylated oxindoles and lactams were obtained in moderate to good yields. (Figure presented.).
- Chen, Chen,Sun, Wan,Yan, Yan,Yang, Fang,Wang, Yuebo,Zhu, Yan-Ping,Liu, Liying,Zhu, Bolin
-
supporting information
p. 2970 - 2975
(2020/07/06)
-
- Chemo- And Regioselective Magnesium-Catalyzed ortho-Alkenylation of Anilines
-
A simple and efficient catalytic system for a chemo- and regioselective ortho-alkenylation of anilines is presented. The new magnesium-catalyzed reaction allows the use of a wide range of alkynes and anilines with different electronic and steric propertie
- Chatupheeraphat, Adisak,Rueping, Magnus,Magre, Marc
-
supporting information
p. 9153 - 9157
(2019/11/14)
-
- Transition-Metal-Free Desulfinative Cross-Coupling of Heteroaryl Sulfinates with Grignard Reagents
-
A mild cross-coupling reaction of heteroaryl sulfinates with Grignard reagents has been developed under transition-metal-free conditions. This study provides an example of the SO22- as a leaving group in an aromatic system and an effective methodology for the construction of C-C bond.
- Wei, Jun,Liang, Huamin,Ni, Chuanfa,Sheng, Rong,Hu, Jinbo
-
supporting information
(2019/02/05)
-
- Palladium(II)/Lewis acid cocatalyzed oxidative annulation of 2-alkenylanilines and propargylic esters: An access to benzo[ b]azepines
-
An attractive approach to valuable yet synthetically challenging benzo[b]azepines was established via palladium(II)/Lewis acid cocatalyzed oxidative [5 + 2] annulation of readily available 2-alkenylanilines and propargylic esters. The protocol features mild reaction conditions and good functional group tolerance, constituting an array of benzo[b]azepines in yields of 30-75%.
- Qiao, Hong,Zhang, Shengjun,Li, Kangkang,Cao, Zhengqiang,Zeng, Fanlong
-
p. 10843 - 10851
(2019/09/12)
-
- Iron-Promoted Construction of Indoles via Intramolecular Oxidative C-N Coupling of 2-Alkenylanilines Using Persulfate
-
Indole scaffold synthesis relies primarily on oxidative C-H amination of N-protected alkenylanilines for C-N intramolecular cyclization reactions. Herein, for the first time, without N-protection, various readily prepared 2-alkenylanilines were transformed into the desired indole products in good yields by using K 2 S 2 O 8 as oxidant in the presence of catalytic amounts of FeF 2. The K 2 S 2 O 8 /FeF 2 system offers a direct and benign synthetic route to 3-arylindoles and it is applicable to a wide range of substituted indoles including drug intermediates.
- Li, Yudong,Li, Yuehui,Luo, Shuping,Wang, Menglan,Wu, Qing-An
-
p. 3085 - 3090
(2019/08/07)
-
- Catalyst-free and selective trifluoromethylative cyclization of acryloanilides using PhICF3Cl
-
Trifluoromethylation-triggered cyclization of alkenes provides a useful route to CF3-containing cyclic compounds. Current approaches to generate CF3-based initiators from a CF3 source require a catalyst or an activator. This work describes a catalyst-free protocol to innately produce electrophilic CF3 species from PhICF3Cl for trifluoromethylative cyclization of acryloanilides. A new domino biscyclization of dienes has been developed leading to trifluoroethylated tetrahydroindenoquinolinones with chemo- and stereo-selectivity.
- Guo, Jia,Xu, Cong,Wang, Ling,Huang, Wanqiao,Wang, Mang
-
supporting information
p. 4593 - 4599
(2019/05/17)
-
- Palladium-catalyzed cascade reactions of alkene-tethered carbamoyl chlorides with: N-tosyl hydrazones: Synthesis of alkene-functionalized oxindoles
-
A palladium-catalyzed cascade reaction of alkene-tethered carbamoyl chlorides with N-tosyl hydrazones is described. It provided a new way to synthesize various alkene-functionalized oxindoles bearing an all-carbon quaternary center. The olefin moieties co
- Sun, Wan,Chen, Chen,Qi, Yuan,Zhao, Jinghui,Bao, Yinwei,Zhu, Bolin
-
supporting information
p. 8358 - 8363
(2019/09/30)
-
- Enantioselective Copper-Catalyzed Borylative Cyclization with Cyclic Imides
-
An enantioselective borylative cyclization cascade utilizing cyclic imides has been developed. We employ a highly enantioselective borylcupration process that includes a 1,2-addition to a cyclic imide. The products contain a valuable hemiaminal and boronate handle for further elaborations within a congested framework. This work demonstrates the utility of cyclic imides as simple precursors to unlock access to sought-after polycyclic indolines. Futhermore, this report highlights the capability to harness reactive catalytic intermediates to exploit otherwise unreactive functional groups.
- Whyte, Andrew,Torelli, Alexa,Mirabi, Bijan,Lautens, Mark
-
supporting information
p. 8373 - 8377
(2019/10/14)
-
- Cleavage of C-C Bonds for the Synthesis of C2-Substituted Quinolines and Indoles by Catalyst-Controlled Tandem Annulation of 2-Vinylanilines and Alkynoates
-
The strategy for the synthesis of C2-substituted indoles and quinolines from 2-vinylanilines and alkynoates through C-C bond cleavage is developed. With these general methods, 2-substituted indoles and quinolines can be accessed via tandem Michael addition and cyclization with no requirement of oxidant. This strategy not only provides a method for the synthesis C2-substituted indoles in good yields through the simultaneous cleavage of C=C and C=C bonds under metal-free conditions but also provides a simple method for the generation of the C2-substituted quinolines in moderate yields via Pd-catalyzed C=C bond cleavage.
- Ni, Jixiang,Jiang, Yong,An, Zhenyu,Yan, Rulong
-
supporting information
p. 1534 - 1537
(2018/03/23)
-
- Base-catalyzed thio-lactamization of 2-(1-arylvinyl)anilines with CS2 for the synthesis of quinoline-2-thiones
-
Here we show that the base-catalyzed thio-lactamization of 2-(1-arylvinyl)anilines with CS2 is a powerful methodology to synthesize quinoline-2-thiones. This thio-lactamization uses inexpensive and versatile 2-(1-arylvinyl)anilines, which are easily available from the reaction of amines and alkynes. Compared to the known strategy in the literature, this method features the advantages like a short synthesis step and easily available starting materials.
- Wang, Tong-Lin,Liu, Xiao-Jun,Huo, Cong-De,Wang, Xi-Cun,Quan, Zheng-Jun
-
supporting information
p. 499 - 502
(2018/01/19)
-
- Base-controlled chemoselectivity reaction of vinylanilines with isothiocyanates for synthesis of quinolino-2-thione and 2-aminoquinoline derivatives
-
Here, we report a base-controlled chemo-selective reaction of vinylanilines with alkyl/aryl isothiocyanates to afford quinolino-2-thione and 2-aminoquinoline derivatives. The quinolino-2-thiones could be obtained in high yields in the presence of Et3N. Particularly interesting is that the reaction could produce the 2-aminoquinolines in the presence of K3PO4 with high selectivity.
- Zhang, Xi,Wang, Tong-Lin,Huo, Cong-De,Wang, Xi-Cun,Quan, Zheng-Jun
-
supporting information
p. 3114 - 3117
(2018/03/28)
-
- Synthesis of 2-Quinolinones via a Hypervalent Iodine(III)-Mediated Intramolecular Decarboxylative Heck-Type Reaction at Room Temperature
-
A hypervalent iodine(III)-mediated intramolecular decarboxylative Heck-type reaction of 2-vinyl-phenyl oxamic acids has been developed. The unique ring-strain-enabled radical decarboxylation mechanism is preliminarily revealed. This protocol features metal-free reaction conditions and operational simplicity, allowing the lactamization of 2-vinylanilines using a readily accessible carbonyl source and the synthesis of various 2-quinolinones with excellent chemoselectivity at room temperature.
- Fan, Huaqiang,Pan, Peng,Zhang, Yongqiang,Wang, Wei
-
supporting information
p. 7929 - 7932
(2019/01/04)
-
- Visible-Light Photocatalytic Decarboxylative Alkyl Radical Addition Cascade for Synthesis of Benzazepine Derivatives
-
A visible-light photocatalytic decarboxylative alkyl radical addition cascade reaction of acrylamide-tethered styrenes for the synthesis of benzazepine derivatives is described. This protocol features broad substrate scope, excellent functional group tolerance, and mild reaction conditions, affording the seven-membered rings in good yields. This method was also applied for efficient grafting of the benzazepine scaffold into the pharmaceutically active ursolic acid scaffold.
- Zhao, Yu,Chen, Jia-Rong,Xiao, Wen-Jing
-
supporting information
p. 224 - 227
(2018/01/17)
-
- Enantioselective Intramolecular Copper-Catalyzed Borylacylation
-
An enantioselective copper-catalyzed intramolecular borylacylation is reported. The reaction proceeds through an initial enantioselective borylcupration of the styrene, followed by a nucleophilic attack on the tethered carbamoyl chloride. The products, chiral borylated 3,3-disubstituted oxindoles, were generated in excellent yields and enantioselectivities. The versatile carbon–boron bond provides a platform for a wide array of diversification.
- Whyte, Andrew,Burton, Katherine I.,Zhang, Jingli,Lautens, Mark
-
supporting information
p. 13927 - 13930
(2018/10/02)
-
- Tert -Butyl nitrite (TBN) as the N atom source for the synthesis of substituted cinnolines with 2-vinylanilines and a relevant mechanism was studied
-
A green method to synthesize cinnolines by 6π electrocyclic reaction with alkenyl amines and TBN has been developed. TBN plays a dual role both as a nitrogen atom source and an oxidant in this procedure. Relevant mechanism experiments reveal that the reaction proceeds through electrocyclic reaction and with diazo hydroxide as a key intermediate.
- Pang, Xiaobo,Zhao, Lianbiao,Zhou, Dagang,He, Ping Yong,An, Zhenyu,Ni, Ji Xiang,Yan, Rulong
-
supporting information
p. 6318 - 6322
(2017/08/10)
-
- Copper-mediated intramolecular aza-Wacker-type cyclization of 2-alkenylanilines toward 3-aryl indoles
-
A copper-mediated intramolecular aza-Wacker-type cyclization was developed for the direct and efficient synthesis of 3-aryl indoles using 2-alkenylanilines in moderate to good yields with good functional group compatibility. This strategy shows the high efficiency, operational simplicity as well as broad substrate scope.
- Yang, Rui,Yu, Jin-Tao,Sun, Song,Zheng, Qingheng,Cheng, Jiang
-
supporting information
p. 445 - 448
(2017/01/11)
-
- Carbon annulation of ortho-vinylanilines with dimethyl sulfoxide to access 4-aryl quinolines
-
A palladium-catalyzed annulation of ortho-vinylanilines with dimethyl sulfoxide was developed to access 4-aryl quinolines in moderate to good yields. Activated by 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO), DMSO served as a “=CH-” fragment in this transformation. It represents a facile pathway leading to 4-aryl quinolines.
- Yuan, Jin,Yu, Jin-Tao,Jiang, Yan,Cheng, Jiang
-
supporting information
p. 1334 - 1337
(2017/02/15)
-
- Synthesis of Indoles from 2-Vinylanilines with PIFA or TFA and Quinones
-
The cyclizations involved in the synthesis of different indoles from 2-vinylanilines with PIFA {[bis(trifluoroacetoxy)iodo]benzene} and quinones have been developed under mild conditions. Various substituents on 2-vinylanilines induced good compatibility and gave the desired products in moderate to good yields.
- Wu, Mingzhong,Yan, Rulong
-
supporting information
p. 729 - 733
(2017/03/21)
-
- Palladium-Catalyzed Domino Alkenylation/Amination/Pyridination Reactions of 2-Vinylanilines with Alkynes: Access to Cyclopentaquinolines
-
A novel domino oxidative annulation of 2-vinylanilines with internal alkynes was developed to constitute a rare class of cyclopentaquinoline derivatives. This transformation encompasses four σ bonds formation, one quaternary carbon center construction, and pyridination steps in one pot under identical conditions, which fascinatingly increases the molecular complexity from easily available starting materials.
- Li, Dejun,Zeng, Fanlong
-
supporting information
p. 6498 - 6501
(2017/12/26)
-
- Copper-catalyzed tandem aerobic oxidative cyclization for the ynthesis of polysubstituted quinolines via C(sp3)/C(sp2)-H bond functionalization
-
One-pot Cu-catalyzed tandem aerobic oxidative cyclization for the synthesis of quinolines from 2-vinylanilines/ 2-arylanilines and 2-methylquinolines via C(sp3)-H/C(sp2)- H bond functionalization has been developed. Dioxygen as an ideal oxidant has been employed for this transformation. The substrates bearing various functional groups perform well in this process and generate the desired products in moderate to good yields.
- Pang, Xiaobo,Wu, Mingzhong,Ni, Jixiang,Zhang, Fuming,Lan, Jingfeng,Chen, Baohua,Yan, Rulong
-
p. 10110 - 10120
(2018/05/31)
-
- Beyond a Protecting Reagent: DMAP-Catalyzed Cyclization of Boc-Anhydride with 2-Alkenylanilines
-
A novel rapid synthesis of quinolines from 2-alkenylanilines has been described; the reaction involves an unexpected DMAP-catalyzed cyclization of 2-alkenylanilines with di-tert-butyl dicarbonate (Boc2O, 2.0 equiv), and a series of tert-butyl quinolin-2-yl carbonate with various functional groups have been synthesized in good yields under mild conditions. Furthermore, the tert-butyl quinolin-2-yl carbonate can be easily converted into corresponding quinolinones and 2-(pseudo)haloquinolines.
- Huang, Ya-Nan,Li, Yin-Long,Li, Jian,Deng, Jun
-
p. 4645 - 4653
(2016/07/06)
-
- Br?nsted Acid-Catalyzed Synthesis of N-Arylindoles from 2-Vinylanilines and Quinones
-
In the presence of a quinone, Br?nsted acid-catalyzed intramolecular C?N bond formation of o-vinylanilines by electrophilic cyclization was developed, giving the corresponding N-arylindoles in good to high yields. The reaction worked well for o-vinylanilines with terminal and internal C=C double bonds.
- Zhang, Han-Ming,Gao, Zhong-Hua,Yi, Liang,Ye, Song
-
supporting information
p. 2671 - 2674
(2016/10/11)
-
- Pd-Catalyzed Intramolecular Heck Reaction, C(sp2)-H Activation, 1,4-Pd Migration, and Aminopalladation: Chemoselective Synthesis of Dihydroindeno[1,2,3-kl]acridines and 3-Arylindoles
-
Palladium-catalyzed intramolecular Heck reaction and aminopalladation of N-(2-(1-phenylvinyl)phenyl)aniline for the efficient synthesis of dihydroindeno[1,2,3-kl]acridines and 3-arylindoles via tuning of the phosphine ligands and solvents under two optimized conditions are reported. The reaction follows a 1,4-Pd migration, aminopalladation, C(sp2)-H activation, as well as five- and six-membered-ring fusion to form different products. The dihydroindeno[1,2,3-kl]acridine derivatives showed higher triplet energy (ET) levels than common blue phosphorescent dopant and may serve as good host candidates for blue triplet emitters.
- Gu, Zheng-Yang,Liu, Cheng-Guo,Wang, Shun-Yi,Ji, Shun-Jun
-
supporting information
p. 2379 - 2382
(2016/06/09)
-
- Ortho-Alkenylation of anilines with aromatic terminal alkynes over nanosized zeolite beta
-
A simple, efficient and environmentally benign catalytic system has been successfully developed for highly regioselective electrophilic alkenylation of anilines with aromatic terminal alkynes over nanosized zeolite beta, which exhibits the highest catalyt
- Mameda, Naresh,Peraka, Swamy,Kodumuri, Srujana,Chevella, Durgaiah,Marri, Mahender Reddy,Nama, Narender
-
p. 78374 - 78378
(2015/09/28)
-
- Palladium-catalyzed direct coupling of 2-vinylanilines and isocyanides: An efficient synthesis of 2-aminoquinolines
-
Palladium-catalyzed oxidative coupling of 2-vinylanilines and isocyanides constitutes a direct, facile, and efficient approach to 2-aminoquinolines. The procedure, employing palladium acetate and silver carbonate, is attractive in terms of assembly efficiency, functional group tolerance, and operational simplicity. A variety of 2-aminoquinolines were prepared in good to excellent yields.
- Wang, Lijie,Ferguson, Jamie,Zeng, Fanlong
-
supporting information
p. 11486 - 11491
(2015/12/04)
-
- Synthesis of benzazetine derivatives by intramolecular iodoamination of o-(acylamino)styrene derivatives
-
The iodoamination of o-(acylamino)styrene derivatives using iodine and sodium hydrogencarbonate, producing 7-acyl-8-iodomethylbicyclo[4.2.0]-7-azaoct- 1,3,5-triene [1-acyl-2-(iodomethyl)benzazetine] derivatives, is described. Replacement of the iodo moiety by hydrogen or phenylthio group is also reported.
- Kobayashi, Kazuhiro,Miyamoto, Kazuna,Morikawa, Osamu,Konishi, Hisatoshi
-
p. 886 - 889
(2007/10/03)
-
- Regioselective electrophilic alkylation of anilines with phenylacetylene in the presence of montmorillonite KSF
-
Substituted anilines react with phenylacetylene in the presence of montmorillonite KSF affording 1,1-diarylethylenes 3 in good yields and excellent selectivities. In the presence of an excess of phenylacetylene. para-toluidine and para-anisidine give the
- Arienti, Attilio,Bigi, Franca,Maggi, Raimondo,Marzi, Elena,Moggi, Pietro,Rastelli, Massimo,Sartori, Giovanni,Tarantola, Fabio
-
p. 3795 - 3804
(2007/10/03)
-