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1.
Afsaneh Feiz Ghazaleh Imani Shakibaei Zahra Yasaei Hamid Reza Khavasi Ayoob Bazgir 《Helvetica chimica acta》2011,94(9):1628-1637
A new four‐component synthesis of spiro[4H‐indeno[1,2‐b]pyridine‐4,3′‐[3H]indoles] and spiro[acenaphthylene‐1(2H),4′‐[4H‐indeno[1,2‐b]pyridines] by the reaction of indane‐1,3‐dione, 1,3‐dicarbonyl compounds, isatins (=1H‐indole‐2,3‐diones) or acenaphthylene‐1,2‐dione, and AcONH4 in refluxing toluene in the presence of a catalytic amount of pyridine is reported. 相似文献
2.
Organocatalytic Asymmetric Cascade Reactions of 7‐Vinylindoles: Diastereo‐ and Enantioselective Synthesis of C7‐Functionalized Indoles
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Prof. Dr. Feng Shi Hong‐Hao Zhang Xiao‐Xue Sun Jing Liang Tao Fan Prof. Shu‐Jiang Tu 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(8):3465-3471
The first catalytic asymmetric cascade reaction of 7‐vinylindoles has been established by the rational design of such substrates. Cascade reactions with isatin‐derived 3‐indolylmethanols in the presence of a chiral phosphoric acid derivative allow the diastereo‐ and enantioselective synthesis of C7‐functionalized indoles as well as the construction of cyclopenta[b]indole and spirooxindole frameworks (all >95:5 d.r., 94–>99 % ee). This approach not only addresses the great challenge of the catalytic asymmetric synthesis of C7‐functionalized indoles, but also provides an efficient method for constructing biologically important cyclopenta[b]indole and spirooxindole scaffolds with excellent optical purity. Investigation of the reaction pathway and activation mode has suggested that this cascade reaction proceeds through a vinylogous Michael addition/Friedel–Crafts process, in which dual H‐bonding activation of the two reactants plays a crucial role. 相似文献
3.
Lianbao Ye Yuanxin Tian Zhonghuang Li Jiajie Zhang Shuguang Wu 《Helvetica chimica acta》2012,95(2):320-326
Since deregulation of the tyrosine‐kinase receptor c‐Met is implicated in several human cancers and is an attractive target for small‐molecule‐drug discovery, we report herein the synthesis of 2,3,4,5‐tetrahydro‐8‐[1‐(quinolin‐6‐ylmethyl)‐1H‐1,2,3‐triazolo[4,5‐b]pyrazin‐6‐yl]‐1H‐pyrido[4,3‐b]indoles 4a – 4c and 2,3,4,5‐tetrahydro‐8‐[3‐(quinolin‐6‐ylmethyl)‐1,2,4‐triazolo[4,3‐b]pyridazin‐6‐yl]‐1H‐pyrido[4,3‐b]indoles 5a – 5c . These indole derivatives demonstrated inhibition of c‐Met kinase activity. Concurrently, five key intermediates were synthesized. These compounds could be prepared in good yields. 相似文献
4.
C. Montagne N. Laurent B. Joseph J.‐Y. Mrour 《Journal of heterocyclic chemistry》2005,42(7):1433-1441
Preparation of the 5‐substituted azepino[3,4‐b]indole core structure can be realised through a catalytic Heck reaction. The scope and limitations of this methodology are reported. The reactivity of di‐tert‐butyl 5‐ethoxycarbonylmethylene‐1,3,4,5‐tetrahydro‐1‐oxoazepino[3,4‐b]indole‐2,10‐dicarboxylate (1) was investigated in order to prepare the indole analogue of hymenialdisine and derivatives. 相似文献
5.
Alireza Hasaninejad Nooshin Golzar Mohsen Shekouhy Abdolkarim Zare 《Helvetica chimica acta》2011,94(12):2289-2294
A sequential one‐pot four‐component reaction for the efficient synthesis of novel 2′‐aminospiro[11H‐indeno[1,2‐b]quinoxaline‐11,4′‐[4H]pyran] derivatives 5 in the presence of AcONH4 as a neutral, inexpensive, and dually activating catalyst is described (Scheme 1). The syntheses are achieved by reacting ninhydrin ( 1 ) with benzene‐1,2‐diamines 2 to give indenoquinoxalines, which are trapped in situ by malono derivatives 2 and various α‐methylenecarbonyl compounds 4 through cyclization, providing the multifunctionalized 2′‐aminospiro[11H‐indeno[1,2‐b]quinoxaline‐11,4′‐[4H]pyran] analogs 5 . This chemistry provides an efficient and promising synthetic way of proceeding for the diversity‐oriented construction of the spiro[indenoquinoxalino‐pyran] skeleton. 相似文献
6.
Efficient One‐Pot Solvent‐Free Synthesis of 1H‐Pyrazolo[1,2‐b]phthalazine‐5,10‐diones Catalyzed by Sulfonic Acid Functionalized Nanoporous Silica (SBA‐Pr‐SO3H)
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Ghodsi Mohammadi Ziarani Nina Hosseini Mohtasham Alireza Badiei Negar Lashgari 《中国化学会会志》2014,61(9):990-994
A green protocol has been developed for the synthesis of 1H‐pyrazolo[1,2‐b]phthalazine‐5,10‐diones by one‐pot cyclocondensation reaction of phthalhydrazide, aromatic aldehydes, and malononitrile or ethyl cyanoacetate using sulfonic acid functionalized SBA‐15 (SBA‐Pr‐SO3H) as a heterogeneous solid acid catalyst under solvent‐free conditions. 相似文献
7.
8.
Yukiko Hayashi Prof. Dr. Yoshihiro Matano Kayo Suda Prof. Dr. Yoshifumi Kimura Prof. Dr. Yoshihide Nakao Prof. Dr. Hiroshi Imahori 《Chemistry (Weinheim an der Bergstrasse, Germany)》2012,18(50):15972-15983
The first comprehensive study of the synthesis and structure–property relationships of 2,2′‐bis(benzo[b]phosphole)s and 2,2′‐benzo[b]phosphole–benzo[b]heterole hybrid π systems is reported. 2‐Bromobenzo[b]phosphole P‐oxide underwent copper‐assisted homocoupling (Ullmann coupling) and palladium‐catalyzed cross‐coupling (Stille coupling) to give new classes of benzo[b]phosphole derivatives. The benzo[b]phosphole–benzo[b]thiophene and ‐indole derivatives were further converted to P,X‐bridged terphenylenes (X=S, N) by a palladium‐catalyzed oxidative cycloaddition reaction with 4‐octyne through the Cβ? H activation. X‐ray analyses of three compounds showed that the benzo[b]phosphole‐benzo[b]heterole derivatives have coplanar π planes as a result of the effective conjugation through inter‐ring C? C bonds. The π–π* transition energies and redox potentials of the cis and trans isomers of bis(benzo[b]phosphole) P‐oxide are very close to each other, suggesting that their optical and electrochemical properties are little affected by the relative stereochemistry at the two phosphorus atoms. The optical properties of the benzo[b]phosphole–benzo[b]heterole hybrids are highly dependent on the benzo[b]heterole subunits. Steady‐state UV/Vis absorption/fluorescence spectroscopy, fluorescence lifetime measurements, and theoretical calculations of the non‐fused and acetylene‐fused benzo[b]phosphole–benzo[b]heterole π systems revealed that their emissive excited states consist of two different conformers in rapid equilibrium. 相似文献
9.
Antonio Da Settimo Anna María Marini Giampaolo Primofiore Federico Da Settimo Silvia Salerno Francesca Simorini Gianluca Pardi Concettina La Motta Daniele Bertini 《Journal of heterocyclic chemistry》2002,39(5):1001-1006
The synthesis of new pyrido[3′,2′:5,6]thiopyrano[3,2‐b]indol‐5(6H)‐ones was accomplished by the Fischer‐indole cyclization of some 2,3‐dihydro‐3‐phenylhydrazonothiopyrano[2,3‐b]pyridin‐4(4H)‐ones, obtained from the 2,3‐dihydro‐3‐hydroxymethylenethiopyrano[2,3‐b]pyridin‐4(4H)‐one, by the Japp‐Klingemann reaction. 6H‐Pyrido[3′,2′:5,6]thiopyrano[4,3‐b]quinolines were obtained by reaction of 2,3‐dihydrothiopyrano‐[2,3‐b]pyridin‐4(4H)‐ones with o‐aminobenzaldehyde or 5‐substituted isatins. The preparation of some derivatives, functionalized with an alkylamino‐substituted side chain, is also described. 相似文献
10.
Antonio Da Settimo Anna Maria Marini Giampaolo Primofiore Federico Da Settimo Silvia Salerno Concettina La Motta Gianluca Pardi Pier Luigi Ferrarini Claudio Mori 《Journal of heterocyclic chemistry》2000,37(2):379-382
The synthesis of the title compounds 5H, 11H‐pyrido[2′,3′:2,3]thiopyrano[4,3‐b]indoles was accomplished by the Fischer indole cyclization of some 2,3‐dihydrothiopyrano[2,3‐b]pyridin‐4(4H)‐one phenylhydrazones and 7‐methyl‐2,3‐dihydrothiopyrano[2,3‐b]pyridin‐4(4H)‐one phenylhydrazones. The synthesis of the new 2,3‐dihydrothiopyrano[2,3‐b]pyridin‐4(4H)‐one, which was used as one of the starting compounds, is also described. 相似文献
11.
Various approaches to the synthesis of 1,4‐dihydropyrrolo[3,2‐b]pyrroles are summarized. Many two‐ and three‐step reaction sequences have been developed, and have allowed access to a broad variety of structures, including not only the parent 1,4‐dihydropyrrolo[3,2‐b]pyrroles, but also their π‐expanded analogues. The newest approaches are critically compared with older strategies. The reactivity of these compounds is also reviewed, with special emphasis on electrophilic aromatic substitution. The synthesis of indolo[3,2‐b]indole derivatives has been the subject of intense investigation. Overall, a few interesting and ingenious approaches toward these ladder‐type heteroacenes have been proposed, reaching total yields in the region of 30 %. Finally, the optical, electrochemical, and other physicochemical properties are presented in the broader perspective of heteropentalenes. The parent 1,4‐dihydro‐pyrrolo[3,2‐b]pyrroles constitute the most electron‐rich, simple, aromatic heterocycles, and their simple derivatives and π‐expanded analogues possess strong violet, blue, or green fluorescence both in solution and in the solid state. 相似文献
12.
An Efficient Synthesis of Spiro‐oxindole Derivatives by Three‐Component Reactions in Water
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An efficient synthesis of (3S)‐1,1′,2,2′,3′,4′,6′,7′‐octahydro‐9′‐nitro‐2,6′‐dioxospiro[3H‐indole‐3,8′‐[8H]pyrido[1,2‐a]pyrimidine]‐7′‐carbonitrile is achieved via a three‐component reaction of isatin, ethyl cyanoacetate, and 1,2,3,4,5,6‐hexahydro‐2‐(nitromethylidene)pyrimidine. The present method does not involve any hazardous organic solvents or catalysts. Also the synthesis of ethyl 6′‐amino‐1,1′,2,2′,3′,4′‐hexahydro‐9′‐nitro‐2‐oxospiro[3H‐indole‐3,8′‐[8H]pyrido[1,2‐a]pyrimidine]‐7′‐carboxylates in high yields, at reflux, using a catalytic amount of piperidine, is described. The structures were confirmed spectroscopically (IR, 1H‐ and 13C‐NMR, and EI‐MS data) and by elemental analyses. A plausible mechanism for this reaction is proposed (Scheme 2). 相似文献
13.
Zhenhang Xu Yijun Du Songxiang Wang Zeru Wu Yuhao Lou Furen Zhang 《Journal of heterocyclic chemistry》2019,56(9):2517-2527
An efficient four‐component approach for the synthesis poly‐substituted pyrano[3,2‐c]pyridones and spiro[indoline‐3,4′‐pyrano[3,2‐c]pyridine]‐2,5′(6′H)‐diones in water has been established. During the reaction, the products were readily achieved through one‐pot two‐step reaction using solid acid as catalyst. The advantages of atom and step economy, the recyclability of heterogeneous solid acid catalyst, easy workup procedure, and the wide scope of substrates make the reaction a powerful tool for assembling pyrano[3,2‐c]pyridone skeletons of chemical and medical interest. 相似文献
14.
Stereoselective [3+2] Carbocyclization of Indole‐Derived Imines and Electron‐Rich Alkenes: A Divergent Synthesis of Cyclopenta[b]indole or Tetrahydroquinoline Derivatives
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Alicia Galván Dr. Jonás Calleja Dr. Adán B. González‐Pérez Prof. Dr. Rosana Álvarez Prof. Dr. Angel R. de Lera Prof. Dr. Francisco J. Fañanás Prof. Félix Rodríguez 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(47):16769-16774
An unprecedented stereoselective [3+2] carbocyclization reaction of indole‐2‐carboxaldehydes, anilines, and electron‐rich alkenes to obtain cyclopenta[b]indoles is disclosed. This pathway is different from the well‐established Povarov reaction: the formal [4+2] cycloaddition involving the same components, which affords tetrahydroquinolines. Moreover, by simply changing the Brønsted acid catalyst, this multicomponent coupling process could be divergently directed towards the conventional Povarov pathway to produce tetrahydroquinolines or to the new pathway (anti‐Povarov) to generate cyclopenta[b]indoles. Supported by computational studies, a stepwise Mannich/Friedel–Crafts cascade is proposed for the new anti‐Povarov reaction, whereas a concerted [4+2] cycloaddition mechanism is proposed for the Povarov reaction. 相似文献
15.
Palladium‐Catalyzed Domino CH/NH Functionalization: An Efficient Approach to Nitrogen‐Bridged Heteroacenes
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Natsuyo Kamimoto Dr. Dieter Schollmeyer Dr. Koichi Mitsudo Prof.Dr. Seiji Suga Prof.Dr. Siegfried R. Waldvogel 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(22):8257-8261
Palladium‐catalyzed domino C?H/N?H functionalization for the synthesis of novel nitrogen‐bridged thienoacenes and 10H‐benzo[4,5]thieno[3,2‐b]indole derivatives from dihaloarene is reported. This domino sequence consists of initial C?H functionalization of the benzo[b]thiophene moiety, followed by Buchwald–Hartwig coupling. This transformation is also useful for the synthesis of highly π‐extended compounds. 相似文献
16.
《Journal of heterocyclic chemistry》2018,55(4):1061-1068
Indolo[3,2‐b]carbazole is a molecule of great biological significance, as it is formed in vivo after consumption of cruciferous vegetables. The reaction of 1H‐indole and various aldehydes in the presence of a catalytic amount of N,2‐dibromo‐6‐chloro‐3,4‐dihydro‐2H‐benzo[e][1,2,4]thiadiazine‐7‐sulfonamide 1,1‐dioxide as an efficient and homogeneous catalyst in acetonitrile at 50°C produces 6,12‐disubstituted 5,7‐dihydroindolo[2,3‐b]carbazole with an in good to excellent yield. The presented technique offers a fast and robust method, by the use of inexpensive commercially available starting materials toward 6,12‐disubstituted 5,7‐dihydroindolo[2,3‐b]carbazole. A new anomeric‐based oxidation was kept in mind for the final step of the indolo[2,3‐b]carbazoles synthesis. The suggested anomeric‐based oxidation mechanism was supported by experimental and theoretical evidences. 相似文献
17.
N‐Heterocyclic Carbene‐Catalyzed Enantioselective Annulation of Indolin‐3‐ones with Bromoenals
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Qijian Ni Xiaoxiao Song Prof. Dr. Gerhard Raabe Prof. Dr. Dieter Enders 《化学:亚洲杂志》2014,9(6):1535-1538
N‐Heterocyclic carbene‐catalyzed reactions of indolin‐3‐ones with 2‐bromoenals opened an asymmetric access to 3,4‐dihydropyrano[3,2‐b]indol‐2(5 H)‐ones in good yields and with good to excellent enantioselectivities. This protocol tolerates a broad substrate scope. In addition, a possible mechanism for the annulation reaction is presented. 相似文献
18.
Polypyrrole/Fe3O4/CNT as a recyclable and highly efficient catalyst for one‐pot three‐component synthesis of pyran derivatives
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Polypyrrole (PPY)/Fe3O4/CNT has been synthesized and characterized by FT‐IR, TEM and SEM techniques and its catalytic activity has been evaluated in the synthesis of several series of pyran derivatives. Tetrahydrobenzo[b]pyranes, 4H‐pyran‐3‐carboxylates, 4H,5H‐pyrano[3,2‐c]chromenes and dihydropyrano[2,3‐c]pyrazoles have been successfully prepared from one‐pot three‐component condensation of aldehyde, malononitrile and active methylene‐containing compounds (dimedone /ethyl acetoacetate/4‐hydroxycoumarin/3‐methyl‐2‐pyrazoline‐5‐one) using PPY/Fe3O4/CNT as a new and reusable heterogeneous catalyst. The present method offer several advantages such as; high yields of products, short reaction times, easy work‐up procedure and easy separation of the catalyst from the reaction mixture due to its magnetic character. Furthermore, chemoselective synthesis of bis‐benzo[b]pyran from terephthalaldehyde can be achieved by this method. 相似文献
19.
Philipp Biegger Manuel Schaffroth Christian Patze Olena Tverskoy Dr. Frank Rominger Prof. Uwe H. F. Bunz 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(19):7048-7052
We describe the efficient synthesis of substituted benzo[3,4]cyclobuta[1,2‐b]phenazine, benzo[3,4]cyclobuta[1,2]benzo[1,2‐i]phenazine, and benzo[3,4]cyclobuta[1,2‐b]naphtho[2,3‐i]phenazine by a condensation reaction of aromatic diamines with the stable biphenylene‐2,3‐dione. 相似文献
20.
Pd‐Catalyzed Cyclocarbonylation of 2‐(2‐Bromoaryl)indoles with CO as a C1 Source: Selective Access to 6 H‐Isoindolo[2,1‐a]indol‐6‐ones and Indeno[1,2‐b]indol‐10(5 H)‐ones
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A highly efficient and regioselective synthetic route to 6 H‐isoindolo[2,1‐a]indol‐6‐ones and indeno[1,2‐b]indol‐10(5 H)‐ones through the Pd‐catalyzed cyclocarbonylation of 2‐(2‐bromoaryl)indoles under atmospheric CO pressure has been achieved. Notably, the regioselectivity of the reaction was exclusively dependent on the structural characteristics of the indole substrates. With N‐unsubstituted indoles as the starting materials, the reaction afforded 6H‐isoindolo[2,1‐a]indol‐6‐ones in good‐to‐excellent yields. On the other hand, with N‐substituted indoles as the substrates, the reaction gave indeno[1,2‐b]indol‐10(5 H)‐ones in a highly regioselective manner. 相似文献