- Efficient one pot synthesis of chromenonaphthyridine derivatives by CuI/InCl3 catalyzed aza diels-alder reaction
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A mild and efficient method for the synthesis of chromenonaphthyridine derivatives via domino reaction of aminopyridine and different O-propargylated salicylaldehydes using CuI/InCl3 as an efficient catalyst, refluxed in acetonitrile is reported. Mild rea
- Maji, Pradip Kumar,Mahalanobish, Ayan
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- Synthesis and biological properties of novel 1-methyl-2-(2-(prop-2-yn-1-yloxy)benzylidene) hydrazine analogues
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1-Methyl-2-(2-(prop-2-yn-1-yloxy)benzylidene)hydrazine analogues were readily prepared in good yields by the reaction of 2-(prop-2-yn-1-yloxy)benzaldehydes and methyl hydrazine. The reaction tolerates a variety of substituents on the 2-hydroxybenzaldehyde
- Kivrak, Arif,Yilmaz, Can,Konus, Metin,Koca, Halil,Aydemir, Selahattin,Oagaz, Jeger Ali
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- Synthesis of coumarin-sulfonamide derivatives and determination of their cytotoxicity, carbonic anhydrase inhibitory and molecular docking studies
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Carbonic anhydrases isoforms CA IX, and XII are known to be highly expressed in various human tissues and malignancies. CA IX is a prominent target for especially colorectal cancers, because it is overexpressed in colorectal cancer and this overexpression
- Zengin Kurt, Belma,Sonmez, Fatih,Ozturk, Dilek,Akdemir, Atilla,Angeli, Andrea,Supuran, Claudiu T.
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- Synthesis of new benzo[f]imidazo[1,2-d][1,4]oxazepines: AgNO3-mediated intramolecular hydroamination
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Novel benzo[f]imidazo[1,2-d][1,4]oxazepine derivatives were synthesized from [4,5-diaryl-2-(2-(prop-2-yn-1-yloxy)aryl)-1H-imidazoles] by a AgNO3-promoted 7-exo-dig hydroamination proceeding in DMF at 80 °C.
- Mahdavi, Mohammad,Hariri, Roshanak,Saeedi, Mina,Foroumadi, Alireza,Shafiee, Abbas,Akbarzadeh, Tahmineh
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- Efficient synthesis of novel 1, 2, 3-triazole-based diazepam derivatives by click CuAAC reaction: Spectroscopic characterizations and DFT studies
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A new family of 1, 2, 3-triazole-based benzodiazepines have been synthesized by the Huisgen [3+2] dipolar cycloaddition reaction of diazepam with O-propargyl salicylaldehydes in the aqueous medium. Mild reaction conditions, excellent yields (70–98%), envi
- Esmaeeli, Zohreh,Khodabakhshi, Mohammad Reza,Mirjafary, Zohreh,Saeidian, Hamid
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- Coumarin-1,2,3-triazole hybrid derivatives: Green synthesis and DFT calculations
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A series of new 1,2,3-triazole-coumarin hybrid system are synthesized from the click reaction between 3-azido coumarin and different aromatic terminal alkyne derivatives in a green manner. All compounds are characterized by IR, NMR and UV–VIS spectroscopy
- Nouraie, Pegah,Moradi Dehaghi, Shahram,Foroumadi, Alireza
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- Synthesis and spectral study of a new family of 2,5-diaryltriazoles having restricted rotation of the 5-aryl substituent
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Efficient synthesis of 2,5-diaryl substituted 4-azido-1,2,3-triazoles by the reaction of sodium azide with dichlorosubstituted diazadienes was demonstrated. The optical properties of the prepared azidotriazoles were studied to reveal a luminescence maximu
- Tsyrenova, Biligma,Nenajdenko, Valentine
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- Synthesis of Novel 7-methylene-6,7-dihyrobenzo[f]Benzo[4,5]Imidazo[1,2-d][1,4]Oxazepines via Base-mediated Regioselective Intramolecular Hydroamination
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A versatile and transition metal-free approach for the synthesis of new 7-methylene-6,7-dihyrobenzo[f]benzo[4,5]imidazo[1,2-d][1,4]oxazepines were developed by an efficient 7-exo-dig regioselective hydroamination of 2-(2-(prop-2-yn-1-yloxy)phenyl)-1H-benzo[d]imidazole in the presence of potassium carbonate in DMF at 90°C.
- Yavari, Hossein,Alinezhad, Heshmatollah,Shafiee, Abbas
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- Synthesis and evaluation of novel triazoles and mannich bases functionalized 1,4-dihydropyridine as angiotensin converting enzyme (ACE) inhibitors
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A series of novel diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate embedded triazole and mannich bases were synthesized, and evaluated for their angiotensin converting enzyme (ACE) inhibitory activity. Screening of above synthesized compounds fo
- Kumbhare, Ravindra M.,Kosurkar, Umesh B.,Bagul, Pankaj K.,Kanwal, Abhinav,Appalanaidu,Dadmal, Tulshiram L.,Banerjee, Sanjay Kumar
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- Synthesis, characterization, PASS prediction and in silico ADME studies of ester and ether linked 1,4-disubstituted 1,2,3-triazoles derivatives via click approach
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In the present investigation, we focused our interest on the synthesis of pharmacophoric units (quinoline and 1,2,3-triazole) linked through ester (3a-b) and (substituted aromatic ring and 1,2,3-triazole) linked through an ether (3c-h). The synthesis invo
- Krishnaswamy,Raghuram Shetty,Roopa,Banu, Salma,Preritha,Rajeshwari,Ravikumar,Pruthviraj,Aruna Kumar,Sreenivasa
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- Copper-catalyzed intramolecular domino synthesis of 6H-chromeno[4,3-b]quinolines in green condition
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A one-pot and efficient copper-catalyzed approach for synthesis of tetracyclic 6H-chromeno[4,3-b]quinolines through the intramolecular domino condensation-aza-Diels-Alder reaction of electron-rich anilines and Opropargylated salicylaldehydes under green conditions has been described.
- Rahimzadeh, Golnaz,Soheilizad, Mehdi,Kianmehr, Ebrahim,Larijani, Bagher,Mahdavic, Mohammad
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- Synthesis of fused nine-membered rings: A simple protocol for synthesis of [1,2,3]-triazolo-[1,4]-benzoxazonine frameworks from the Baylis-Hillman acetates
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A simple and facile protocol for synthesis of tricyclic [1,2,3]-triazolo-[1,4]-benzoxazonine derivatives has been developed from the Baylis-Hillman acetates by treatment with sodium azide followed by heating the resulting azido-alkyne in toluene under ref
- Basavaiah, Deevi,Reddy, Bhavanam Sekhara,Lingam, Harathi
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- Copper(I)-Catalyzed Intramolecular Cyclization of o-Propargyloxy Diketopiperazines to Access Diverse Diazabicyclic and Spiro-Diketopiperazinochromanes
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In this report, two distinctive intramolecular cyclizations of o-propargyloxy diketopiperazines (achieved from a one-pot Ugi post-transformation) is achieved via a copper(I)-catalyzed intramolecular reaction of azomethine ylide and alkyne moiety. The presence of internal alkyne in the starting materials directed the reaction towards through [3+2]-cycloaddition, while terminal alkyne led to a spirocyclization reaction between azomethine ylide and terminal unsaturated C?C bond. This method offering an opportunity for the synthesis of challenging Diazabicyclics and Spiro-Diketopiperazinochromanes in high yields with exclusive diastereoselectivity. (Figure presented.).
- Armaghan, Mahsa,Balalaie, Saeed,Bijanzadeh, Hamid Reza,Frank, Walter,Manavi, Bita,Rominger, Frank,Tejeneki, Hossein Zahedian
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supporting information
p. 4190 - 4196
(2021/08/06)
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- CuI/Cu(OSO2CF3)2 catalysed convenient approach to dichromenopyridines and triazole-thiazole appended chromone derivatives
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A variety of new pentacyclic dichromenopyridines have been synthesized from 2-amino chromone and O-propargyloxy salicilaldehydes through intramolecular Povarov reaction using CuI/Cu(OSO2CF3)2 as a Lewis acid catalyst. The
- Yerrabelly, Jayaprakash Rao,Porala, Subbanarasimhulu,Kasireddy, Venkateshwar Reddy,Ghojala, Venkat Reddy,Rebelli, Pradeep
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p. 3781 - 3790
(2021/11/01)
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- 1,2,3-Triazole-linked 5-benzylidene (thio)barbiturates as novel tyrosinase inhibitors and free-radical scavengers
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In this study, benzyl-1,2,3-triazole-linked 5-benzylidene (thio)barbiturate derivatives 7a–d and 8a–h were designed as potential tyrosinase inhibitors and free-radical scavengers. The twelve derivatives were synthesized via the [3+2] cycloaddition reactio
- Ranjbar, Sara,Shahvaran, Parisa-sadat,Edraki, Najmeh,Khoshneviszadeh, Mahsima,Darroudi, Mahdieh,Sarrafi, Yaghoub,Hamzehloueian, Mahshid,Khoshneviszadeh, Mehdi
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- Gold-catalyzed formation of aryl-fused pyrazolooxazepines via intramolecular regioselective 7-exo-dig cyclization
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An efficient method was developed for the synthesis of substituted aryl-fused pyrazolooxazepines from ortho-O-propargyl aryl pyrazoles by gold catalysis. In this organic transformation a new C-N bond was formed regioselectively via 7-exo-dig cyclization.
- Guduru, Ravinder,Mangina, N. S. V. M. Rao,Sridhar, Balasubramanian,Karunakar, Galla V.
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supporting information
p. 2809 - 2817
(2019/03/12)
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- “On water” cascade synthesis of benzopyranopyrazoles and their macrocycles
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Reported herein is an intramolecular 1,3-dipolar cycloaddition strategy for rapid entry into benzopyranopyrazoles (BPP) on water medium as “open flask chemistry” approach. The in situ generation of diazo functionality in two-step sequence from the appropr
- Muthusamy, Sengodagounder,Gangadurai, Chinnakuzhanthai
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supporting information
p. 1501 - 1505
(2018/03/21)
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- Development of 13H-benzo[f]chromeno[4,3-b][1,7]naphthyridines and their salts as potent cytotoxic agents and topoisomerase I/IIα inhibitors
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A novel series of 35 angularly fused pentacyclic 13H-benzo[f]chromeno[4,3-b][1,7]naphthyridines and 13H-benzo[f]chromeno[4,3-b][1,7]naphthyridin-5-ium chlorides were designed and synthesized. Their cytotoxic activities were investigated against six human
- Arepalli, Sateesh Kumar,Lee, Chaerim,Sim, Seongrak,Lee, Kiho,Jo, Hyunji,Jun, Kyu-Yeon,Kwon, Youngjoo,Kang, Jong-Soon,Jung, Jae-Kyung,Lee, Heesoon
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supporting information
p. 5181 - 5193
(2018/10/02)
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- A Discrete Self-Assembled Pd12 Triangular Orthobicupola Cage and its Use for Intramolecular Cycloaddition
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Water-soluble Pd12L6 coordination cage TC-1 was synthesized by coordination-driven self-assembly of symmetrical tetrapyridyl donor L with 90° ditopic acceptor cis-[Pd(NO3)2(tmeda)] [tmeda=N,N,N′,N′-tetramethylet
- Bhat, Imtiyaz Ahmad,Devaraj, Anthonisamy,Zangrando, Ennio,Mukherjee, Partha Sarathi
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p. 13938 - 13946
(2018/09/06)
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- A facile one-pot regioselective synthesis of functionalized novel benzo[f]chromeno[4,3-b][1,7]naphthyridines and benzo[f][1,7]naphthyridines via an imino Diels-Alder reaction
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A novel series of functionalized 13H-benzo[f]chromeno[4,3-b][1,7]naphthyridines and 1,3-diphenylbenzo[f][1,7]naphthyridines have been synthesized by an efficient regioselective one-pot multicomponent synthesis through intra and intermolecular imino Diels-
- Arepalli, Sateesh Kumar,Park, Byeongwoo,Jung, Jae-Kyung,Lee, Kiho,Lee, Heesoon
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supporting information
p. 449 - 454
(2017/01/10)
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- Microwave-Assisted Organocatalytic Intramolecular Knoevenagel/Hetero Diels-Alder Reaction with O-(Arylpropynyloxy)-Salicylaldehydes: Synthesis of Polycyclic Embelin Derivatives
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A highly efficient and regioselective approach to new polycyclic embelin derivatives through a domino Knoevenagel condensation/intramolecular hetero Diels-Alder reaction using O-(arylpropynyloxy)-salicylaldehydes in the presence of ethylenediamine diacetate (EDDA) is reported. This organocatalyzed protocol is compatible toward a wide range of aryl-substituted alkynyl ethers with electron-donating and electron-withdrawing groups. When other active methylene compounds were subjected to this domino reaction the corresponding adducts were obtained in high yield.
- Martín-Acosta, Pedro,Feresin, Gabriela,Tapia, Alejandro,Estévez-Braun, Ana
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p. 9738 - 9756
(2016/11/02)
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- Synthesis, DNA binding affinity and anticancer activity of novel 4: H -benzo [g] [1,2,3]triazolo[5,1- c] [1,4]oxazocines
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A new class of tricyclic heterocycles 4H-benzo[g][1,2,3]triazolo[5,1-c][1,4]oxazocines was synthesized through a Knoevenagel condensation/azide-alkyne cycloaddition reaction cascade in one-pot operation. These eight membered ring containing heterocycles exhibited moderately high anticancer activity against four cancer cell lines; human cervix cancer cell line (HeLa), human prostate cancer cell line (DU145), human breast cancer cell line (MCF-7) and human breast adenocarcinoma epithelial cell line (MDA-MB-231). Our results indicate that these compounds have a weak cytotoxic effect on normal human mammary epithelial cell line (MCF-10A). Cell cycle and apoptosis assay indicate that they inhibit the cell cycle at the G2/M phase and induce apoptosis. Through the RED100 assay, it is evident that they have potential to inhibit pBR 322 plasmid DNA cleavage by BamH1. UV-visible, fluorescence titration and viscosity studies suggested that these compounds possess DNA binding affinity.
- Sastry, K. N. Visweswara,Routhu, Sunitha Rani,Datta, Soma Gupta,Nagesh, Narayana,Babu, Bathini Nagendra,Nanubolu, Jagadeesh Babu,Kumar, C. Ganesh,Maurya, Ram Awatar,Kamal, Ahmed
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p. 9294 - 9305
(2016/10/13)
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- [Et3NH][HSO4]-catalyzed one-pot, solvent-free synthesis and biological evaluation of α-amino phosphonates
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Abstract: A series of dimethyl (phenyl(phenylamino)methyl)phosphonates and novel dimethyl ((phenylamino)(2-(prop-2-yn-1-yloxy)phenyl)methyl)phosphonates as potential antifungal agents were synthesized via one-pot, three-component condensation of aldehydes, amines and trimethyl phosphite in solvent-free conditions using [Et3NH][HSO4] as an efficient, eco-friendly and reusable catalyst. Compared to other methods, this new method consistently has advantages, including excellent yields, a short reaction time, mild reaction conditions and catalyst reusability. The newly synthesized propargylated ether containing α-amino phosphonates were evaluated for antifungal and antioxidant activity and were also analyzed for absorption, distribution, metabolism and excretion (ADME) properties. Graphical Abstract: [Figure not available: see fulltext.]
- Shaikh, Mubarak H.,Subhedar, Dnyaneshwar D.,Kalam Khan, Firoz A.,Sangshetti, Jaiprakash N.,Shingate, Bapurao B.
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p. 5115 - 5131
(2016/07/06)
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- Synthesis and in vitro antibacterial evaluation of novel 4-substituted 1-menthyl-1,2,3-triazoles
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Menthyl 1,4-disubstituted 1,2,3-triazole derivatives of hydroxybenzaldehydes, phenols and bile acids were synthesized via click chemistry. The novel synthesized compounds were evaluated for their in vitro antibacterial activity against Enterococcus faeciu
- Khaligh, Pooneh,Salehi, Peyman,Bararjanian, Morteza,Aliahmadi, Atousa,Khavasi, Hamid Reza,Nejad-Ebrahimi, Samad
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p. 1589 - 1596
(2016/11/09)
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- An improved synthesis of natural product inspired chromenopyrrolizines and chromenoindolizines scaffolds: Rapid access to the diverse pyrrolizine analogs of aza-medicarpin and tetracyclic isolamellarin core through a general base and metal free strategy
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An improved synthesis for easy access to the natural product inspired chromenopyrrolizine and chromenoindolizine scaffolds is delineated. The strategy involves controlled thermal activation of diverse salicylaldehyde tethered dipolarophiles having the str
- Khan, Tabrez,Kumar, Virendra,Das, Oindreela
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supporting information
p. 1331 - 1340
(2017/08/02)
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- Intramolecular heterocyclization of o -propargylated aromatic hydroxyaldehydes as an expedient route to substituted chromenopyridines under metal-free conditions
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A concise and regioselective approach to the synthesis of chromenopyridine and chromenopyridinone derivatives was developed. The synthetic strategy relies on the O-propargylation of aromatic hydroxyaldehydes followed by reaction with propargylamine. The i
- Keskin, Selbi,Balci, Metin
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supporting information
p. 964 - 967
(2015/03/18)
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- Trifluoroethanol as an efficient reaction media for the synthesis of pyran skeleton through domino Knoevenagel-hetero-Diels-Alder reaction with non-activated alkynes
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Trifluoroethanol as an efficient media for the domino Knoevenagel-hetero-Diels-Alder reaction of O-propargyloxy benzaldehydes as non-activated terminal alkynes with some active methylene compounds has been described. Short reaction time, easy work-up, good to high yields, and mild reaction conditions are advantages of this new media. Graphical Abstract: [Figure not available: see fulltext.]
- Balalaie, Saeed,Azizian, Javad,Shameli, Abolghasem,Bijanzadeh, Hamid Reza
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p. 631 - 637
(2015/02/19)
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- Nucleophilic addition of amines to ruthenium carbenes: Ortho-(alkynyloxy)benzylamine cyclizations towards 1,3-benzoxazines
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A new ruthenium-catalyzed cyclization of ortho-(alkynyloxy)benzylamines to dihydro-1,3-benzoxazines is reported. The cyclization is thought to take place via the vinyl ruthenium carbene intermediates which are easily formed from [CpRuCl(cod)] and N2CHSiMe3. The mild reaction conditions and the efficiency of the procedure allow the easy preparation of a broad range of new 2-vinyl-2-substituted 1,3-benzoxazine derivatives. Rearrangement of an internal C(sp) in the starting material into a tetrasubstituted C(sp3) atom in the final 1,3-benzoxazine is highly remarkable.
- Gonzlez-Rodrguez, Carlos,Surez, Jos Ramn,Varela, Jess A.,Sa, Carlos
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supporting information
p. 2724 - 2728
(2015/03/04)
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- Unprecedented synthesis of aza-bridged benzodioxepine derivatives through a tandem Rh(ii)-catalyzed 1,3-rearrangement/[3+2] cycloaddition of carbonyltriazoles
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Rh(ii)-catalyzed novel tandem intramolecular cycloisomerizations of aldehydes or ketones with 1-sulfonyl 1,2,3-triazoles have been disclosed, providing a facile protocol to access a series of functionalized aza-bridged benzodioxepine heterocycles.
- Zhang, Yong-Sheng,Tang, Xiang-Ying,Shi, Min
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supporting information
p. 15971 - 15974
(2015/01/08)
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- An efficient synthesis of 2H-chromen-3-yl derivatives via CuI/(NH 4)2HPO4 catalyzed reaction of O-propargyl salicylaldehydes with active methylene compounds
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2H-Chromen-3-yl-methylenemalononitriles/cyanoacrylates/cyanoacrylamides with variant structural features have been serendipitously formed during an endeavour to prepare 5H-chromeno[3,4-c]pyridine using CuI/(NH4) 2HPO4 cata
- Kumari, Kumkum,Raghuvanshi, Dushyant Singh,Singh, Krishna Nand
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- Zirconium oxide (NP) - Ionic liquid as an efficient media for the domino Knoevenagel hetero Diels-Alder reaction with unactivated alkynes
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Immobilized ZrO2-nanopowder (NP) in ionic liquid and different organic solvents was used as a suitable Lewis-acid for the synthesis of polycyclic heterocycles which contains pyran-based skeletons. Reaction of O-propargylated salicylaldehyde wit
- Balalaie, Saeed,Poursaeed, Ali,Khoshkholgh, Malihe Javan,Bijanzadeh, Hamid Reza,Wolf, Eckardt
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body text
p. 283 - 289
(2012/06/30)
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- Catalyst-free synthesis of diversely substituted 6H-benzo[c]chromenes and 6H-benzo[c]chromen-6-ones in aqueous media under MWI
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In this paper, a catalyst-free synthesis of diversely substituted 6H-benzo[c]chromenes and 6H-benzo[c]chromen-8-ols via cascade reactions of 2-(2-(allyloxy)phenyl)furan and 2-(2-(prop-2-ynyloxy)phenyl)furan, featured with intramolecular Diels-Alder reactions of furan with unactivated alkene/alkyne in aqueous media under MWI, was developed. In addition, an environmentally friendly oxidation of 6H-benzo[c]chromenes into the corresponding benzo[c]chromen-6-ones using aqueous H2O2 as an oxidant, in the absence of any activator/catalyst, was also revealed.
- He, Yan,Zhang, Xinying,Cui, Liangyan,Wang, Jianji,Fan, Xuesen
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supporting information
p. 3429 - 3435
(2013/01/16)
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- Regioselective synthesis of chromeno[4′,3′:4,5]pyrano[3,2-c][1, 8]naphthyridin-13-one derivatives by Domino Knoevenagel-Hetero-Diels-Alder reactions
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Efficient synthesis of chromeno[4′,3′:4,5]pyrano[3,2-c][1,8] naphthyridin-13-one derivatives has been described by domino Knoevenagel-hetero-Diels-Alder reaction of 4-hydroxy-1-phenyl-1,8-naphthyridin- 2(1H)-one with O-allylated/propargylated salicylaldehydes. The reaction occurs in a single step and is highly regio- and stereoselective giving polycyclic heterocycles in high yields.
- Majumdar,Taher, Abu,Ponra, Sudipta
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scheme or table
p. 3716 - 3722
(2011/12/16)
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- Dihydro-3 H -chromeno-[3,4- b ][4,7]phenanthrolin-3-one and Chromeno[4,3- b ]pyrano[3,2- f ]quinolin-3(13 H)-one derivatives by aza-Diels-Alder reaction
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Dihydro-3H-chromeno[3,4-b][4,7]phenanthrolin-3-one and chromeno[4,3-b] pyrano[3,2-f]quinolin-3(13H)-one derivatives have been synthesized by aza-Diels-Alder reaction of O-propargylated salicylaldehyde with 6-aminoquinolone and 6-aminocoumarin respectively
- Majumdar,Ponra, Sudipta,Taher, Abu
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scheme or table
p. 463 - 468
(2011/03/20)
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- Regioselective synthesis and structural elucidation of 1,4-disubstituted 1,2,3-triazole derivatives using 1D and 2D NMR spectral techniques
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Regioselective synthesis of 2-[1-(2-oxo-2-phenylethyl)-1H-[1,2,3]triazol-4- ylmethoxy]-benzaldehyde derivatives was achieved by [3 + 2] cycloaddition reaction of 2-(prop)-2-ynyloxy-benzaldehyde derivatives with phenacyl azide. The regiochemistry and the s
- Babu, Thelagathoti Hari,Phani Kumar,Rajeswari,Perumal, Paramasivan T.
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scheme or table
p. 824 - 829
(2012/03/22)
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- N-heterocyclic carbene-catalyzed cascade reaction involving the hydroacylation of unactivated alkynes
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The N-heterocyclic carbene (NHC)-catalyzed hydroacylation of unactivated alkynes to provide α,β-unsaturated ketones is reported. In addition, a rare case of an efficient and selective dually NHC-catalyzed cascade reaction involving the hydroacylation of a
- Biju, Akkattu T.,Wurz, Nathalie E.,Glorius, Frank
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supporting information; experimental part
p. 5970 - 5971
(2010/07/05)
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- Synthesis of isoxazolobenzoxepanes via Michael addition of indoles to nitroalkenes and sequential intramolecular nitrile oxide cycloaddition
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Nitroalkenes derived from O-propargyl salicylaldehyde undergo facile Michael addition with indoles leading to indole-derived Michael adducts. Intramolecular nitrile oxide cycloaddition (INOC) of the Michael adducts results in isoxazolobenzoxepanes in good
- Ramachandiran,Karthikeyan,Muralidharan,Perumal
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scheme or table
p. 3006 - 3009
(2010/07/10)
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- Synthesis of pyrano[3,4-c]chromene skeleton via CuI-mediated domino Knoevenagel hetero-Diels-Alder reaction
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(Chemical Equation Presented) A new strategy involving domino Knoevenagel hetero-Diels-Alder reaction is described for the preparation of pyrano[3,4-c]chromenes scaffold. Reaction of O-propargylated salicylaldehyde with benzoylacetonitrile or Meldrum's ac
- Mollazadeh, Marjan,Khoshkholgh, Malihe Javan,Balalaie, Saeed,Rominger, Frank,Bijanzadeh, Hamid Reza
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body text
p. 1200 - 1208
(2010/11/16)
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- Copper(I)-catalyst-free approach for the synthesis of chromene-fused pyrido[3,2-d]pyrimidines by Lewis acid catalyzed aza-Diels-Alder reaction
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Pyrido[3,2-d]pyrimidine derivatives have been synthesized by the hetero-Diels-Alder reaction of 5-amino-1,3-dimethyl uracil and O-propargylated salicylaldehyde. The reaction requires only a single-step operation and provides potentially bioactive polycycl
- Majumdar,Ponra, Sudipta,Ganai, Sintu
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scheme or table
p. 2575 - 2578
(2010/12/18)
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- Catalyst-free domino-Knoevenagel-hetero-Diels-Alder reaction of terminal alkynes in water: an efficient one-step synthesis of indole-annulated thiopyranobenzopyran derivatives
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The domino-Knoevenagel-hetero-Diels-Alder reaction of O-propargylated salicylaldehyde and 1-methylindoline-2-thione in aqueous medium in the absence of Lewis acid has been described for the synthesis of hitherto unreported indole-annulated pentacyclic het
- Majumdar,Taher, Abu,Ponra, Sudipta
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scheme or table
p. 147 - 150
(2010/03/03)
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- Catalyst-free regioselective synthesis of benzopyran-annulated thiopyrano[2,3-b]thiochromen-5-(4H)-one derivatives by domino-Knoevenagel-hetero-Diels-Alder reaction of terminal alkynes with 4-hydroxy dithiocoumarin in aqueous medium
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The synthesis of novel pentacyclic benzopyran-annulated thiopyrano[2,3-b] thiochromen-5(4H)-ones has been described by domino-Knoevenagel-hetero-Diels-Alder reaction of 4-hydroxy dithiocoumarin and O-propargylated salicylaldehyde in aqueous medium and in
- Majumdar,Taher, Abu,Ponra, Sudipta
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scheme or table
p. 2297 - 2300
(2010/05/18)
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- Green synthesis of benzopyran-annulated thiopyrano[2,3-b ]thiochromen-5(4 H)-ones by domino Knoevenagel-hetero-Diels-Alder reaction
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Benzopyran-annulated thiopyrano[2,3-b]thiochromen-5(4H)-ones have been synthesized by the domino Knoevenagel-hetero-Diels-Alder (DKHDA) reaction of 4-hydroxydithiocoumarin with O-allylated salicylaldehyde and O-propargylated salicylaldehyde in aqueous medium. The reaction requires only a single step operation and is highly regio- and stereoselective providing potentially bioactive polycyclic heterocycles in high yields. Georg Thieme Verlag Stuttgart - New York.
- Majumdar,Taher, Abu,Ponra, Sudipta
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scheme or table
p. 4043 - 4050
(2011/02/22)
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- Anionic cyclization of (N,N-Dimethylamino)[2-(prop-2-yn-1-yloxy)aryl]- acetonitriles
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The cyclization of (N,N-dimethylamino)[2-(prop-2-yn-1-yloxy)aryl] acetonitriles is carried out under phase-transfer conditions using powdered sodium hydroxide and benzyltriethylammonium chloride as catalyst in dimethyl sulfoxide to afford mixtures of a me
- Zdrojewski, Tadeusz,Musielak, Joanna,Jonczyk, Andrzej
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experimental part
p. 2029 - 2034
(2010/01/13)
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- Wittig olefination and thiol mediated 7-endo-trig radical cyclization: novel synthesis of oxepin derivatives
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Thiophenol-mediated 7-endo radical cyclization for the synthesis of seven-membered cyclic ethers is described. This method can be successfully applied to synthesize various benzoxepin derivatives, which are present in many natural products as building blo
- Majumdar,Taher, Abu
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scheme or table
p. 228 - 231
(2009/05/07)
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- Intramolecular hetero-Diels-Alder reaction of 1-oxa-1,3-butadienes with terminal acetylenes in aqueous media using CuI
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A new method for the preparation of tetracyclic uracils (oxa-helicene) 4 was developed. The intramolecular hetero-Diels-Alder reaction of 1-oxa-1,3-butadiene 3 and an unactivated alkyne in the presence of CuI led to tetracyclic uracils 4 in aqueous media
- Khoshkholgh, Malihe Javan,Balalaie, Saeed,Gleiter, Rolf,Rominger, Frank
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p. 10924 - 10929
(2008/12/23)
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- Synthesis of functionalized 1-benzoxepins by tandem ring-opening/ cyclocondensation of 3-bromoisoxazoles
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A series of functionalized 1-benzoxepins were synthesized by way of a tandem ring-opening/cyclocondensation of aldehyde-containing 3-bromoisoxazoles.
- Kociolek, Martin G.,Straub, Nicholas G.,Schuster, Jolene V.
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p. 259 - 262
(2007/10/03)
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- Synthesis of tricyclic aromatic compounds by the intramolecular Pauson-Khand reaction promoted by molecular sieves
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Pauson-Khand reactions are carried out with different substituted aromatic enynes, yielding tricyclic cyclopentenones related to natural products such as chromenes. Enynes are easily obtained in a two-step approximation from the corresponding salicylaldehydes. The reaction is promoted by dissolved TMANO (trimethylamine N-oxide) and/or 4 A molecular sieves. This new way of induction for the Pauson-Khand reaction increases yields remarkably, allowing the reaction of some substituted alkenes which fail to react in the absence of the zeolite. Isomerization of the double bond of the cyclopentenone ring is observed except when nonterminal triple bonds are used. For trisubstituted alkenes, an interrupted Pauson-Khand process is observed with moderate yields.
- Perez-Serrano, Leticia,Blanco-Urgoiti, Jaime,Casarrubios, Luis,Dominguez, Gema,Perez-Castells, Javier
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p. 3513 - 3519
(2007/10/03)
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- (1)BENZOPYRANO(4,3-c)PYRAZOLES BY INTRAMOLECULAR NITRILE IMINE ADDITION TO ACETYLENES
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2-Alkynyloxy-benzaldehydes 1 are obtained by alkylation of the corresponding salicylaldehydes either with p-toluenesulfonic acid propargylester or 1-acetoxy-4-chloro-but-2-yne.The aldehydes 1 are converted into the hydrazones 2 by reaction with p-toluenes
- Janietz, Dietmar,Rudorf, Wolf-Dieter
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p. 1661 - 1666
(2007/10/02)
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