- A new 1,2,3-triazole-decorated imino-phenol: selective sensing of Zn2+, Cu2+and picric acid under different experimental conditions
-
A new 1,2,3-triazole-decorated imino-phenol1has been synthesized, characterized and employed in metal ion sensing. Compound1is weakly fluorescent in CH3CN-H2O (3?:?1, v/v, pH = 6.8, and 10 mM HEPES buffer containing 1% DMSO) and show
- Ghosh, Sumit,Baildya, Nabajyoti,Ghosh, Kumaresh
-
-
Read Online
- Copper-Catalyzed Trifluoromethylation/Cyclization of Alkynes for Synthesis of Dioxodibenzothiazepines
-
A facile and efficient approach for the synthesis of the CF3-containing dioxodibenzothiazepines has been developed via copper-catalyzed trifluoromethylation/cyclization of alkynes utilizing a radical relay strategy. This method has demonstrated low cataly
- Zhang, Zi-Qi,Xu, Yi-Hao,Dai, Jing-Cheng,Li, Yan,Sheng, Jie,Wang, Xi-Sheng
-
supporting information
p. 2194 - 2198
(2021/04/05)
-
- Copper-Catalyzed Enantioselective C-H Arylation between 2-Arylindoles and Hypervalent Iodine Reagents
-
The copper-catalyzed enantioselective C-H arylation between 2-arylindoles and hypervalent iodine reagents has been successfully developed, which provides a convenient and economical route to the highly atroposelective synthesis of axially chiral indole de
- Liang, Hao,Zhu, Guoxun,Pu, Xiaoyun,Qiu, Liqin
-
supporting information
p. 9246 - 9250
(2021/12/06)
-
- Sequential Sonogashira/intramolecular aminopalladation/cross-coupling ofortho-ethynyl-anilines catalyzed by a single palladium source: rapid access to 2,3-diarylindoles
-
We have developed a practical and efficient one-pot protocol for the synthesis of 2,3-diarylindolesviaPd-catalyzed bis-arylative cyclization of variouso-ethynylanilines with aryl iodides. Mechanism studies showed that a Pd-catalyzed Sonogashira reaction took place firstly, giving an internal alkyne intermediate, which subsequently underwent intramolecular aminopalladation/cross-coupling to give access to 2,3-diarylindoles. The present methodology exhibits a broad substrate scope, producing various 2,3-diaryl indoles bearing two different aryl groups.
- Wang, Jiwei,Wang, Gendi,Cheng, Xiang,Liu, Ye,Zhang, Jun
-
supporting information
p. 1329 - 1333
(2021/02/26)
-
- Synthesis of 3-Methylthioindoles via Intramolecular Cyclization of 2-Alkynylanilines Mediated by DMSO/DMSO-d6 and SOCl2
-
The intramolecular cyclization of 2-alkynylanilines mediated by DMSO/SOCl2 was found to afford biologically interesting 3-methylthioindoles, which are rarely obtained by the exiting methods. DMSO could also be replaced with its deuterated count
- Li, Xuemin,Zhang, Beibei,Zhang, Jingran,Wang, Xi,Zhang, Dongke,Du, Yunfei,Zhao, Kang
-
p. 1211 - 1224
(2021/05/04)
-
- Iridium-Catalyzed Isomerization/Cycloisomerization/Aromatization of N-Allyl-N-sulfonyl-o-(λ1-silylethynyl)aniline Derivatives to Give Substituted Indole Derivatives
-
We have developed a one-iridium-catalyst system that transforms N-allyl-N-sulfonyl-2-(silylalkynyl)aniline derivatives, which are 1,7-enynes in which both multiple bonds have a heteroatom, to the corresponding substituted indole derivatives via isomerizat
- Arisawa, Mitsuhiro,Matsuzaki, Tsuyoshi,Murai, Kenichi,Ohno, Shohei,Qiu, Jiawei,Sako, Makoto,Suzuki, Takeyuki,Takehara, Tsunayoshi,Tanaka, Tomoyuki
-
supporting information
p. 4284 - 4288
(2021/06/28)
-
- Photocatalytic Biheterocyclization of 1,7-Diynes for Accessing Skeletally Diverse Tricyclic 2-Pyranones
-
A new and green route to skeletally diverse oxo-heterocyclic architectures such as pyrano[3,4-c]chromen-2-ones and pyrano[3,4-c]quinolin-2-ones is reported via an unprecedented photocatalytic Kharasch-type cyclization/1,5-(SN″)-substitution/elimination/6π
- Wang, Lu,Xu, Ting,Rao, Qian,Zhang, Tian-Shu,Hao, Wen-Juan,Tu, Shu-Jiang,Jiang, Bo
-
supporting information
p. 7845 - 7850
(2021/10/20)
-
- New indolo[1,2-c]quinazolines for single-crystal field-effect transistor: A united experimental and theoretical studies
-
Here, we account the synthesis and characterization of a series of symmetrical fused heterocyclic aromatic hydrocarbons (HAHs) with an indolo[1,2-c]quinazoline (IQ) as the core moiety. All the new HAHs IQ series were systematically investigated by using various spectroscopic methods. Furthermore, their photo-physical properties were supported by density functional theory (DFT) and time-dependent density functional theory (TDDFT) studies to support the experimental findings. The tetramethyl-substituted indolo[1,2-c]quinazoline (TMIQ) compound is shown to exhibit the shifted type of π–π stacking interactions, which render this series as a new semiconducting material. Single-crystal-based field-effect transistor devices of TMIQ exhibited efficient charge transport behavior, giving a p-channel field-effect mobility of 0.25 cm2?V?1?s?1 with an on/off ratio of 5 × 105.
- Puli, Venkat Swamy,Kilaru, Suresh,Bhongiri, Yadagiri,Marri, Sreenath Reddy,Tripathi, Anuj,Chetti, Prabhakar,Chatterjee, Anindita,Vukoti, Kiran Kumar,Pola, Someshwar
-
-
- Photoinduced Radical Cascade Cyclization: A Metal-Free Approach to Access Difluoroalkylated Dioxodibenzothiazepines
-
A simple and mild photoredox catalytic approach to access difluoroalkylated dioxodibenzothiazepines in high regioselectivity via radical cascade cyclization has been described herein. In contrast to previous methods, this strategy does not involve the use
- Deng, Yinglan,Jian, Jing-Xin,Lu, Maojian,Tong, Qing-Xiao,Xiao, Qian,Zhong, Jian-Ji
-
supporting information
p. 9303 - 9308
(2021/12/06)
-
- Solvent-Dependent Cyclization of 2-Alkynylanilines and ClCF2COONa for the Divergent Assembly of N-(Quinolin-2-yl)amides and Quinolin-2(1 H)-ones
-
Herein, we present an expedient Cu-catalyzed [5 + 1] cyclization of 2-alkynylanilines and ClCF2COONa to divergent construction of N-(quinolin-2-yl)amides and quinolin-2(1H)-ones by regulating the reaction solvents. Notably, nitrile acts as a solvent and performs the Ritter reactions. ClCF2COONa is used as a C1 synthon in this transformation, which also represents the first example for utilization of ClCF2COONa as an efficient desiliconization reagent. The current protocol involves in situ generation of isocyanide, copper-activated alkyne, Ritter reaction and protonation.
- Wang, Ya,Zhou, Yao,Ma, Xingxing,Song, Qiuling
-
supporting information
p. 5599 - 5604
(2021/08/01)
-
- Copper-Catalyzed Chemoselective Cyclization Reaction of 2-Isocyanoacetophenone: Synthesis of 4-Hydroxyquinoline Compounds
-
A copper-catalyzed intramolecular cyclization reaction of 2-isocyanoacetophenone derivatives to afford 4-hydroxyquinolines chemoselectively is described. The transformation proceeds through enol tautomerism and a subsequent C-C bond formation. Compared to previous methods, this study provides a new protocol for the construction of 4-hydroxyquinoline compounds from functionalized isocyanides under mild conditions.
- Yuan, Qing,Rao, Weidong,Wang, Shun-Yi,Ji, Shun-Jun
-
supporting information
p. 1279 - 1284
(2020/01/22)
-
- Synthesis of 1H-Pyrrolo[1,2-a]indoles via Lewis Acid-Catalyzed Annulation of Propargylic Alcohols with 2-Ethynylanilines
-
A novel highly efficient, environmentally benign Lewis acid-catalyzed, and protection-free protocol for the construction of valuable polycyclic products bearing a 1H-pyrrolo[1,2-a]indole scaffold is described, starting from readily available propargylic alcohols and 2-ethynylanilines. The one-pot transformation entails the cleavage of one C?O bond, and the construction of two C?N bonds and one C?C double bond. This unique operationally simple method is performed under mild conditions and in air, producing water as the only byproduct; it is scalable and demonstrates good functional group compatibility and broad scope.
- Du, Li-Juan,Han, Ya-Ping,Liang, Yong-Min,Zhang, Hong-Yu,Zhang, Yuecheng,Zhao, Jiquan
-
supporting information
(2020/03/04)
-
- Copper-Catalyzed Tandem Cross-Coupling/[2 + 2] Cycloaddition of 1,6-Allenynes with Diazo Compounds to 3-Azabicyclo[5.2.0] Ring Systems
-
An unprecedented copper-catalyzed tandem cross-coupling/[2 + 2] cycloaddition of 1,6-allenynes with diazo compounds was reported, chemo- and regioselectively providing 3-azabicyclo[5.2.0] frameworks in moderate to excellent yields under mild reaction conditions. Moreover, the products readily convert to highly functionalized quinolines via oxidative radical rearrangement.
- He, Min,Chen, Nuan,Zhou, Ting,Li, Qing,Li, Hongguang,Lang, Ming,Wang, Jian,Peng, Shiyong
-
supporting information
p. 9559 - 9563
(2019/11/21)
-
- Cascade Synthesis of Benzothieno[3,2- b]indoles under Oxidative Conditions Mediated by CuBr and tert-Butyl Hydroperoxide
-
A series of biologically relevant compounds of benzothieno[3,2-b]indole derivatives were conveniently synthesized from reactions of N-protected 2-((2-bromophenyl)ethynyl)anilines and potassium ethylxanthate, mediated by cuprous bromide/tert-butyl hydroper
- Zhao, Xiaoyuan,Li, Qiao,Xu, Jun,Wang, Donghua,Zhang-Negrerie, Daisy,Du, Yunfei
-
supporting information
p. 5933 - 5937
(2018/09/29)
-
- Gold-Catalyzed Intermolecular [4+2] Annulation of 2-Ethynylanilines with Ynamides: An Access to Substituted 2-Aminoquinolines
-
A gold-catalyzed intermolecular [4+2] annulation of easily accessible 2-ethynylanilines with ynamides offers a highly region-selective, modular, efficient, and atom-economical strategy for the synthesis of substituted 2-aminoquinolines in up to 93% yield. (Figure presented.).
- Zhao, Ximei,Song, Xinlong,Jin, Hongming,Zeng, Zhongyi,Wang, Qian,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
-
supporting information
p. 2720 - 2726
(2018/07/29)
-
- Access to Benzo[a]carbazoles and Indeno[1,2-c]quinolines by a Gold(I)-Catalyzed Tunable Domino Cyclization of Difunctional 1,2-Diphenylethynes
-
The cyclization order of the difunctional 1,2-diphenylethynes was precisely tuned under the catalysis of gold by changing the nitrogen substitution of the substrates, leading to the facile preparation of benzo[a]carbazole and indeno[1,2-c]quinoline derivatives. The mechanisms of these domino cyclizations were probed by control experiments, and an insight into the selectivity of the cyclization was gained by density functional theory (DFT) calculations. This research represents a unified and common method to access benzo[a]carbazoles and indeno[1,2-c]quinolines.
- Peng, Xiaoshi,Zhu, Lifeng,Hou, Yuqian,Pang, Yadong,Li, Yangming,Fu, Jiayue,Yang, Lu,Lin, Bin,Liu, Yongxiang,Cheng, Maosheng
-
supporting information
p. 3402 - 3405
(2017/07/15)
-
- Photopromoted Entry to Benzothiophenes, Benzoselenophenes, 3H-Indoles, Isocoumarins, Benzosultams, and (Thio)flavones by Gold-Catalyzed Arylative Heterocyclization of Alkynes
-
Visible light-promoted and gold-photoredox-catalyzed reactions of heteroatom (N, S, Se, O) tethered alkynes with arenediazonium salts selectively proceeded to build vicinal diaryl-substituted 2H-benzo[e][1,2]thiazine 1,1-dioxides (benzosultams), benzoselenophenes, benzothiophenes, 4H-chromen-4-ones (flavones), 3H-indoles, 1H-isochromen-1-ones (isocoumarins), and 4H-thiochromen-4-ones (thioflavones). Moreover, the utility of functionalized 3H-indoles as precursors for further elaboration has been demonstrated with the switchable and facile preparation of 1H-indoles, 2-oxindoles, and 3-oxindolines. (Figure presented.).
- Alcaide, Benito,Almendros, Pedro,Busto, Eduardo,Herrera, Fernando,Lázaro-Milla, Carlos,Luna, Amparo
-
supporting information
p. 2640 - 2652
(2017/08/16)
-
- A dramatic enhancing effect of InBr3 towards the oxidative Sonogashira cross-coupling reaction of 2-ethynylanilines
-
The addition of InBr3 to the oxidative Sonogashira cross-coupling reaction of 2-ethynylaniline with (E)-trimethyl(3,3,3-trifluoroprop-1-enyl)silane led to a dramatic increase in the reactivity to afford the corresponding 1,3-enynes bearing a trifluoromethyl group on their terminal sp2 carbon. The subsequent cyclization of these 1,3-enynes under palladium catalysis provides access to the corresponding indoles bearing a 3,3,3-trifluoroprop-1-enyl group at their 2-position.
- Ikeda,Omote,Kusumoto,Komori,Tarui,Sato,Ando
-
supporting information
p. 2127 - 2133
(2016/02/18)
-
- Revisiting the Gold-Catalyzed Dimerization of 2-Ethynylanilines: A Room-Temperature and Silver-Free Protocol for the Synthesis of Multifunctional Quinolines
-
A room temperature and silver-free protocol for the formation of quinolines from 2-ethynylanilines through a dimerization event was achieved using a dinuclear gold catalyst, Au2(BIPHEP)(NTf2)2. The reaction is inherently modular, allowing for the incorporation of peripheral substituents at any site of the quinoline product. The reaction is readily applied to other heterocyles also as exemplified by the preparation of naphthyridines. Competition reactions to determine the reactivity of dissimilar alkynes demonstrated that the product ratio of dimerization vs intermolecular addition is rather dependent on the electronic nature of aryl substituent on the alkynes. However, control experiments with substrates possessing internal alkynes resulted in cycloisomerization instead of expected dimerization, which is indicative of possible steric influence of the alkyne terminus in the reaction outcome.
- Praveen, Chandrasekar,Perumal
-
p. 855 - 864
(2016/03/15)
-
- Cs2CO3 as a source of carbonyl and ethereal oxygen in a Cu-catalysed cascade synthesis of benzofuran [3,2-: C] quinolin-6[5- H] ones
-
The simultaneous construction of C-C, C-O, and C-N bonds utilizing Cs2CO3 as a source of both carbonyl (CO) and ethereal oxygen and a cascade synthesis of benzofuro[3,2-c]quinolin-6(5H)-one have been achieved using a combination of C
- Ali, Wajid,Modi, Anju,Behera, Ahalya,Mohanta, Prakash Ranjan,Patel, Bhisma K.
-
supporting information
p. 5940 - 5944
(2016/07/06)
-
- One-Pot Access to Benzo[a]carbazoles via Palladium(II)-Catalyzed Hetero- and Carboannulations
-
A Pd(II)-catalyzed direct synthesis of benzo[a]carbazoles has been achieved through aminopalladation of alkynes, followed by intramolecular nucleophilic addition of the generated carbon-palladium bond to a tethered cyano/aldehyde group. Compared to literature procedures, this synthetic approach is operationally simple, uses simple substrates, and offers a fast intramolecular assembly resulting in the direct synthesis of benzo[a]carbazoles in which a wide variation of substituents at different sites is well-tolerated, leaving enough opportunity for diversification.
- Jash, Moumita,Das, Bimolendu,Chowdhury, Chinmay
-
supporting information
p. 10987 - 10999
(2016/11/28)
-
- CuI-Catalyzed intramolecular aminocyanation of terminal alkynes in N-(2-ethynylphenyl)-N-sulfonylcyanamides via Cu-vinylidene intermediates
-
CuI-Catalyzed intramolecular aminocyanation of terminal alkynes in N-(2-ethynylphenyl)-N-sulfonylcyanamides was initiated by the formation of Cu-acetylide to trigger N-CN bond cleavage of the N-sulfonylcyanamide moiety followed by CN migration to form a β-cyano Cu-vinylidene intermediate. Subsequently, the indole ring closure furnished the corresponding 1-sulfonyl-3-cyanoindoles.
- Liao, Zhen-Yuan,Liao, Pen-Yuan,Chien, Tun-Cheng
-
supporting information
p. 14404 - 14407
(2016/12/23)
-
- Copper-catalyzed annulation of α-substituted diazoacetates with 2-ethynylanilines: The direct synthesis of C2-functionalized indoles
-
Copper-catalyzed direct annulation of α-substituted diazoacetates with 2-ethynylanilines leading to C2-functionalized indoles was achieved under mild reaction conditions. The C2-(carboxylate methyl) substituted indoles were obtained in moderate to high yi
- Liu, Gang,Xu, Guangyang,Li, Jian,Ding, Dong,Sun, Jiangtao
-
supporting information
p. 1387 - 1390
(2014/03/21)
-
- [Cp*IrCl2]2 catalyzed formation of 2,2′-biindoles from 2-ethynylanilines
-
[Cp*IrCl2]2 catalyzes the cyclization of 2-ethynylanilines to 2,2′-biindoles via intramolecular hydroamination. A reaction pathway has been proposed on the basis of deuterium labeling experiments and computational studies.
- Kumaran, Elumalai,Fan, Wai Yip,Leong, Weng Kee
-
supporting information
p. 1342 - 1345
(2014/04/03)
-
- Convergent routes to substituted naphthylamides
-
Practical, convergent routes to variously substituted 1- and 2-naphthylamides have been developed. They exploit the ability of xanthates to undergo both intermolecular radical additions to vinyl pivalate and intramolecular radical cyclisations to aromatic
- Tran, Ngoc Diem My,Zard, Samir Z.
-
p. 3251 - 3264
(2014/05/06)
-
- Flexible and practical synthesis of 3-oxyindoles through gold-catalyzed intermolecular oxidation of o-ethynylanilines
-
A novel gold-catalyzed intermolecular oxidation of o-ethynylanilines has been developed. A range of functionalized 3-oxyindoles are readily accessed by utilizing this strategy. Importantly, this gold-catalyzed oxidative process outcompetes the typical ind
- Shu, Chao,Li, Long,Xiao, Xin-Yu,Yu, Yong-Fei,Ping, Yi-Fan,Zhou, Jin-Mei,Ye, Long-Wu
-
supporting information
p. 8689 - 8692
(2014/07/22)
-
- TUNABLE PHENYLACETYLENE HOSTS
-
A compound, or a salt thereof, having the formula wherein Y is n is 1 or 2; each R is independently H, alkyl, substituted alkyl, a polyether moiety, carboxyl, substituted carboxyl, carbamate, substituted carbonate, carbonyloxy, alkoxy, substituted alkoxy,
- -
-
Paragraph 0271
(2014/02/16)
-
- p-Toluenesulfonic acid promoted annulation of 2-alkynylanilines with activated ketones: Efficient synthesis of 4-Alkyl-2, 3-disubstituted quinolines
-
Reactions between readily available 2-alkynylanilines and activated ketones such as ss-keto esters promoted by p-toluenesulfonic acid afford 4-alkyl-2, 3-disubstituted quinolines in good to excellent yields. The generality of substituents at the other end of the triple bond of 2-alkynylanilines makes the method a valuable approach to diversified 4-alkylquinolines, which are difficult to obtain by classical methods such as the Friedlaender reaction. Quinoline dimers can be prepared efficiently with alkyl or aryl linkers at C-4.
- Peng, Changlan,Wang, Yong,Liu, Lanying,Wang, Honggen,Zhao, Jiaji,Zhu, Qiang
-
supporting information; experimental part
p. 818 - 822
(2010/04/02)
-
- Construction of nitrogen heterocycles bearing an aminomethyl group by copper-catalyzed domino three-component coupling-cyclization
-
(Chemical Equation Presented) A direct approach to 2-(aminomethyl)indoles by copper-catalyzed domino three-component coupling-cyclization of 2-ethynylanilines with a secondary amine and aldehyde has been developed. By use of a cyclic or acyclic secondary
- Ohta, Yusuke,Chiba, Hiroaki,Oishi, Shinya,Fujii, Nobutaka,Ohno, Hiroaki
-
supporting information; experimental part
p. 7052 - 7058
(2009/12/06)
-
- InBr3-promoted divergent approach to polysubstituted indoles and quinolines from 2-ethynylanilines: Switch from an intramolecular cyclization to an intermolecular dimerization by a type of terminal substituent group
-
(Chemical Equation Presented) Use of a 2-ethynylaniline having an alkyl or aryl group on the terminal alkyne selectively produced a variety of polyfunctionalized indole derivatives in moderate to excellent yields via indium-catalyzed intramolecular cyclization of the corresponding alkynylaniline. In contrast, employment of a substrate with a trimethylsilyl group or with no substituent group on the terminal triple bond, exclusively afforded polysubstituted quinoline derivatives in good yields via indium-promoted intermolecular dimerization of the ethynylaniline. This indium catalytic system successfully accommodated the intramolecular cyclization of other arylalkyne skeletons involving a carboxylic acid and an amide group.
- Sakai, Norio,Annaka, Kimiyoshi,Fujita, Akiko,Sato, Asuka,Konakahara, Takeo
-
p. 4160 - 4165
(2008/09/21)
-
- Rhodium-catalyzed cycloisomerization: Formation of indoles, benzofurans, and enol lactones
-
(Chemical Equation Presented) Internal affairs: Indoles, benzofurans, and enol lactones are formed chemoselectively from the rhodium-catalyzed cyclo-isomerization reaction of easily prepared alkynyl aniline substrates (see scheme, cod = cycloocta-1,5-diene, DMF = N,N-dimethylformamide). The reaction may proceed by nucleophilic capture of a vinylidene intermediate. Indoles are formed under mild conditions using low catalyst loadings.
- Trost, Barry M.,McClory, Andrew
-
p. 2074 - 2077
(2008/02/14)
-
- Direct synthesis of polysubstituted quinoline derivatives by InBr 3-promoted dimerization of 2-ethynylaniline derivatives
-
InBr3 promotes the dimerization of 2-ethynylaniline derivatives containing an unsubstituted terminal carbon leading to the production of polysubstituted quinoline derivatives in good yield.
- Sakai, Norio,Annaka, Kimiyoshi,Konakahara, Takeo
-
p. 3653 - 3655
(2007/10/03)
-
- Acetonitrile-mediated synthesis of 2,4-dichloroquinoline from 2-ethynylaniline and 2,4-dichloroquinazoline from anthranilonitrile
-
2,4-Dichloroquinolines and 2,4-dichloroquinazolines were synthesized from 2-ethynylanilines and anthranilonitriles, respectively, using diphosgene in acetonitrile and heating at 130 °C or 150 °C for 12 hours. This reaction was applied to the synthesis of 4,6-dichloropyrazolo[3,4-d]pyrimidine (dichloro-9H-isopurine). The postulated mechanism is also described. Georg Thieme Verlag Stuttgart.
- Lee, Jae Hak,Lee, Byoung Se,Shin, Hyunik,Nam, Do Hyun,Chi, Dae Yoon
-
-
- Synthesis of 4H-3,1-Benzoxazines, Quinazolin-2-ones, and Quinoline-4-ones by Palladium-Catalyzed Oxidative Carbonylation of 2-Ethynylaniline Derivatives
-
An effective and straightforward approach to the synthesis of 4H-3,1-benzoxazines 3 and 4, quinazolin-2-ones 5, and quinoline-4-one derivatives 6 and 7 is provided by palladium-catalyzed cyclization-alkoxycarbonylation of variously substituted 2-(trimethy
- Costa, Mirco,Della Ca, Nicola,Gabriele, Bartolo,Massera, Chiara,Salerno, Giuseppe,Soliani, Matteo
-
p. 2469 - 2477
(2007/10/03)
-
- Efficient reagents for the synthesis of 5-, 7-, and 5,7-substituted indoles starting from aromatic amines: Scope and limitations
-
Upon reaction with IPy2BF4, 4-substituted anilines give regioselectively the corresponding o-iodoanilines in nearly quantitative yield, in a process that can be carried out on a multigram scale. Palladium-catalyzed coupling of the resulting 2-iodoanilines with (trimethylsilyl)acetylene (TMSA), followed by efficient CuI-mediated nitrogen cyclization onto alkynes with concurrent elimination of the TMS substituent, allows a straightforward elaboration of 5-mono- and 5,7-disubstituted indoles from aromatic amines. This new approach to the aforementioned indoles does not requires protective groups on nitrogen at any step and can be adapted for preparing related 7-monosubstituted indoles. Moreover, examples iterating the process are given, allowing bis-annulation and sequential double annulation and resulting in synthesis of benzodipyrroles. Additionally, suitable conditions for iodination of some of the target indoles with IPy2BF4 are discussed.
- Ezquerra, Jesus,Pedregal, Concepcion,Lamas, Carlos,Barluenga, Jose,Perez, Marta,Garcia-Martin, Miguel Angel,Gonzalez, Jose M.
-
p. 5804 - 5812
(2007/10/03)
-