- Novel Synthesis of Furoindole Derivatives
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Isatin reacted with diethyl 3-amino-2-cyano-2-pentenedioate in ethanol and in presence of Et3N to give 3-(1-amino-2-cyano-2-ethoxycarbonyl)ethenyl-2H-furoindol-2-one.The reaction of (2-oxo-3-indolinylidene)-malononitrile (3a) with the diethyl ester
- Abd El-Latif, Fathy Faheem,Gohar, Abd El-Kareem Mohammed
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- A convenient route toward one-pot multicomponent synthesis of spirochromenes and pyranopyrazoles accelerated via quinolinic acid
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In the present work, the catalytic activity of quinolinic acid (QUIN) was studied for the synthesis of spirochromene and pyranopyrazole derivatives from readily available materials. The salient features of these one-pot multicomponent protocols are the clean reaction profile, easy isolation of products, no chromatographic separation techniques, high efficiency, short reaction time, and high yield of products plus using QUIN as a new, inexpensive, commercially available, and efficient organocatalyst.
- Oudi, Maryam,Sanchooli Tazeh, Kazem,Hazeri, Nourallah,Fatahpour, Maryam,Ahmadi, Raheleh
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- [bmim]OH: An efficient catalyst for the synthesis of mono and bis spirooxindole derivatives in ethanol at room temperature
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A rapid and efficient, one pot synthesis of spirooxindole derivatives has been attempted by three-component reaction of isatin, malononitrile and carbonyl compound possessing a reactive α-methylene group by using task specific ionic liquid, 1-butyl-3-meth
- Padvi, Swapnil A.,Tayade, Yogesh A.,Wagh, Yogesh B.,Dalal, Dipak S.
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- Preparation and characterization of a novel organic–inorganic hybrid nanostructure: application in synthesis of spirocompounds
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Abstract: Immobilization and heterogenization of acidic/basic groups or organic tags on inorganic supports have found many important applications in recent years. In this investigation, a new hybrid organic–inorganic nanostructure was prepared. The struct
- Ahadi, Najmieh,Bodaghifard, Mohammad Ali,Mobinikhaledi, Akbar
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- Carbon-SO3H: A novel and recyclable solid acid catalyst for the synthesis of spiro[4H-pyran-3,3′-oxindoles]
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A bioglycerol derived carbon-sulfonic acid is found to catalyze efficiently the three-component one-pot condensation of isatin, malononitrile, and 1,3-dicarbonyls to afford a wide range of spiro[4H-pyran-3,3′-oxindole] derivatives in good yields and selec
- Maheshwar Rao,Reddy, G. Niranjan,Reddy, T. Vijaikumar,Devi, B.L.A. Prabhavathi,Prasad,Yadav,Reddy, B.V. Subba
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- Iodine-Catalyzed One-Pot Four-Component Synthesis of Spiro[indoline-3,4′-pyrano-pyrazole] Derivatives
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An efficient, facile, and useful synthetic method was developed for the production of spiro[indoline-3,4′-pyrano-pyrazole] carbonitrile derivatives through a one-pot, four-component reaction involving hydrazine hydrate, diketene, substituted isatins, and malononitrile or ethyl cyanoacetate in the presence of iodine as the efficient catalyst in ethanol at room temperature. Significantly, this remarkable method provides novel spiropyranopyrazole derivatives in good to high yields. The significant aspects of this protocol are facile work-up approach and a greener process because the use of toxic and hazardous solvents are avoided.
- Rezvanian, Atieh,Zadsirjan, Vahideh,Saedi, Pegah,Heravi, Majid M.
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- Cu (II)-β-cyclodextrin complex stabilized on magnetic nanoparticles: A retrievable hybrid promoter for green synthesis of spiropyrans
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The magnetic core of manganese ferrite (MnFe2O4) nanoparticles has a significant stability in comparison with ferrite (Fe3O4) nanoparticles. The unique supramolecular properties of β-cyclodextrin (β-CD), such as
- Ahadi, Najmieh,Bodaghifard, Mohammad Ali,Mobinikhaledi, Akbar
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- Synthesis of spirochromene derivatives catalyzed by Mn(bpyo)2/MCM-41 in water
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A three-component one-pot synthesis of spirochromene derivatives by condensing cyclic 1,3-diketones, isatin or acenaphthenequinone, and malononitrile using a catalytic amount of Mn(bpyo)2/MCM-41 in refluxing water is reported.
- Daraie, Mansoureh,Beheshtiha, Yahya S.,Heravi, Majid M.
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- Ce(III) immobilized on aminated poly(vinyl chloride): high-performance synergistic bifunctional acid–base catalyst for one-pot synthesis of 1,4-dihydropyrano[2,3-c]pyrazoles
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A bifunctional acid–base catalyst of CeIII immobilized on ethylenediamine (EDA)-grafted poly(vinyl chloride) (PVC) has been prepared by a simple approach. First, PVC was treated with EDA to afford aminated poly(vinyl chloride) (PVC–EDA). Therea
- Zhang, Tianzhu,Zhou, Junbin,Chen, Yang,Li, Yiqun
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- Synthesis of a novel DABCO-based nanomagnetic catalyst with sulfonic acid tags: application to the synthesis of diverse spiropyrans
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Abstract: In this paper, sulfonic acid functionalized 1,4-diazabicyclo[2.2.2]octane (DABCO)-based magnetic nanoparticle Fe3O4 [Fe3O4@SiO2@Pr-DABCO-SO3H]Cl2 was synthesized and fu
- Rajabi-Salek, Mostafa,Zolfigol, Mohammad Ali,Zarei, Mahmoud
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- Non-catalytic thermal multicomponent assembling of isatin, cyclic CH-acids and malononitrile: An efficient approach to spirooxindole scaffold
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Thermal non-catalytic reaction of isatin, cyclic CH-acids and malononitrile in water or alcohols affords substituted spirooxindoles in 90-97% yields.
- Elinson, Michail N.,Ilovaisky, Alexey I.,Merkulova, Valentina M.,Zaimovskaya, Tatiana A.,Nikishin, Gennady I.
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- Oleic acid: A benign Br?nsted acidic catalyst for densely substituted indole derivative synthesis
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Oleic acid was identified to catalyse bis(indolyl)methane and densely functionalized 4H-chromene, spirooxindole and spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] derivative synthesis in good to excellent yields. The synergy between Br?nsted acidity and surfa
- Ganesan, Asaithampi,Kothandapani, Jagatheeswaran,Nanubolu, Jagadeesh Babu,Ganesan, Subramaniapillai Selva
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- Meglumine promoted one-pot, four-component synthesis of pyranopyrazole derivatives
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Meglumine, a bio-based chemical, was demonstrated to be a highly efficient and reusable catalyst for the synthesis of a series of pyranopyrazole derivatives via a one-pot, four-component reaction of carbonyl compound or isatin, hydrazine hydrate, malononi
- Guo, Rui-Yun,An, Zhi-Min,Mo, Li-Ping,Yang, Shu-Tao,Liu, Hong-Xia,Wang, Shu-Xia,Zhang, Zhan-Hui
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- Tris-hydroxymethylaminomethane (THAM): An efficient organocatalyst in diversity-oriented and environmentally benign synthesis of spirochromenes
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Tris-hydroxymethylaminomethane has been demonstrated to be an efficient organocatalyst in diversity-oriented synthesis of medicinally prevalent spirochromenes by one-pot, three-component reactions between isatins, malononitrile, and enolizable C–H acids l
- Khot, Supriya S.,Anbhule, Prashant V.,Desai, Uday V.,Wadgaonkar, Prakash P.
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- N-Sulfonic acid modified poly(styrene-co-maleic anhydride): An efficient and recyclable solid acid catalyst for the synthesis of a wide range of spiropyrans
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N-Sulfonic acid modified poly(styrene-co-maleic anhydride) as a recyclable solid acid catalyst efficiently catalyzed the one-pot three-component synthesis of spiropyran derivatives through a simple, convenient, and cost-effective approach in good yields a
- Heravi, Majid M.,Hashemi, Elaheh,Azimian, Fereshteh
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- Bovine serum albumin: An efficient and green biocatalyst for the one-pot four-component synthesis of pyrano[2,3-c]pyrazoles
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The use of biocatalysts is attracting an increasing amount of attention in chemical catalysis. Here, we have shown that bovine serum albumin (BSA), a ubiquitous, inexpensive, non-enzymatic transport protein, can serve as an efficient, retrievable catalyst
- Huang, Xingtian,Li, Zhipeng,Wang, Dongyang,Li, Yiqun
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- Alpha-Casein: an efficient, green, novel, and eco-friendly catalyst for one-pot multi-component synthesis of bis (pyrazol-5-ols), dihydro-pyrano[2,3-c]pyrazoles and spiropyranopyrazoles in an environmentally benign manner
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For the first time, alpha-Casein was used as an efficient and eco-friendly catalyst for an effective and facile preparation of dihydropyranopyrazoles and spiropyranopyrazoles. The synthesis of bis (pyrazol-5-ols) derivatives was developed via one-pot, pseudo-five-component condensation, and the target dihydropyrano[2,3-c]pyrazoles and spiropyranopyrazoles were prepared by one-pot four-component reaction. This new method of employing alpha-Casein, which is a green, recyclable, non-toxic and commercially available catalyst, offers advantages such as mild condition, short reaction times, easy work-up, no need for column chromatography, and high yields of the products which make it more economic than other environmentally synthetic protocols.
- Milani, Jalili,Maghsoodlou, Malek Taher,Hazeri, Nourallah,Nassiri, Mahmoud
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- Novel organometallic nanomagnetic catalyst for multicomponent synthesis of spiroindoline derivatives
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A novel, green, reusable polyaniline (PANI)/Fe3O4/carbon nanotube (CNT) nanomagnetic catalyst has been prepared, characterized by Fourier-transform infrared (FT-IR) spectroscopy, transmission electron microscopy (TEM), and X-ray diff
- Hojati, Seyedeh Fatemeh,Amiri, Amirhassan,Mohamadi, Sakineh,MoeiniEghbali, Nasrin
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- Supported palladium oxide nanoparticles in Al-SBA-15 as an efficient and reusable catalyst for the synthesis of pyranopyrazole and benzylpyrazolyl coumarin derivatives via multicomponent reactions
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An eco-friendly method for diversity-oriented synthesis of substituted dihydropyrano[2,3-c]pyrazole and benzylpyrazolyl coumarin derivatives has been achieved via one-pot and multicomponent reaction in the presence of PdO/Al-SBA-15 as an efficient and rec
- Heravi, Majid M.,Malakooti, Reihaneh,Kafshdarzadeh, Kosar,Amiri, Zahra,Zadsirjan, Vahideh,Atashin, Hassan
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p. 203 - 234
(2022/01/19)
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- An efficient one pot four-component synthesis of spiro[indoline-3,4′pyrano[2,3-c]pyrazole] derivatives via electrochemical approach
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An efficient, simple and one pot, synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] derivative by electrochemically induced condensation of β-keto ester, hydrazine hydrate, malononitrile or ethyl cyanoacetate and isatin in an undivided cell at const
- Upadhyay, Abhishek,Singh
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p. 1685 - 1691
(2021/07/02)
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- Preparation of GO/SiO2/PEA as a new solid base catalyst for the green synthesis of some spirooxindole derivatives
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Efficient and green one pot multi component synthesis of some spirooxindole derivatives in the presence of graphene oxide functionalized with 2-(1-piperazinyl) ethylamine (GO/SiO2/PEA) as a solid base catalyst was studied. GO/SiO2/PEA has been obtained through a two step reaction and characterized by Fourier transform infrared spectroscopy (FTIR), field emission scanning electron microscopy (FE-SEM), energy-dispersive X-ray spectroscopy (EDX), thermo gravimetric analysis (TGA), Raman spectroscopy and X-ray diffraction (XRD). Green reaction conditions, short reaction times, reusable catalyst and a high to excellent yield of products are some of the advantageous of the presented method.
- Moradi, Leila,Toorbaf, Mahla
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p. 21840 - 21850
(2021/07/01)
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- The one-pot four-component eco-friendly synthesis of spirooxindoles in deep eutectic solvent
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Abstract: An efficient and facile synthesis of spirooxindole derivatives bearing pyrano[2,3-c]pyrazole moiety has been achieved using deep eutectic solvent (DES) promoting a four-component reaction. The protocol avoids the use of costly and toxic catalyst
- Devi, Thokchom Jeeta,Singh, Thokchom Prasanta,Singh, Okram Mukherjee
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- CsF promoted rapid synthesis of spirooxindole-pyran annulated heterocycles at room temperature in ethanol
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A newer, versatile, and straightforward synthetic strategy for the construction of functionalized spirooxindole-pyran annulated heterocycles is described. The procedure is based on CsF-promoted rapid tandem Knoevenagel-Michael-Cyclocondensation reaction o
- Dalal, Dipak S.,Mahulikar, Pramod P.,Padvi, Swapnil A.,Wagh, Yogesh B.
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- A ternary hybrid system based on combination of mesoporous silica, heteropolyacid and double-layered clay: an efficient catalyst for the synthesis of 2,4-dihydro-3H-pyrazol-3-ones and pyranopyrazoles in aqueous medium: studying the effect of the synthetic
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SBA/hydrotalcite/heteropolyacid nanocomposite is synthesized via a novel procedure in which the as-prepared heteropolyacid-loaded SBA-15 was impregnated with calcined hydrotalcite. The ternary hybrid system was characterized by using SEM/EDS, XRD, BET, TP
- Sadjadi, Samahe,Heravi, Majid M.,Zadsirjan, Vahideh,Farzaneh, Vahid
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p. 6765 - 6785
(2018/07/13)
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- Aspirin: an efficient catalyst for synthesis of bis (pyrazol-5-ols), dihydropyrano[2,3-c]pyrazoles and spiropyranopyrazoles in an environmentally benign manner
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Abstract: This article aimed to present two facile and environmental friendly routes for the rapid assembly of?biologically active compounds including pyrazol core using aspirin as a novel and green catalyst. The synthesis of bis(pyrazol-5-ol) derivatives was developed via one-pot, pseudo-five-component condensation, and the target dihydropyrano[2,3-c]pyrazoles and spiropyranopyrazoles were prepared by one-pot, four-component reaction. These reactions can be performed in tandem from readily available starting materials. The main merits of the present methods are operational simplicity, no need for column chromatography, inexpensive materials, avoidance of harmless and corrosive acid catalysts, short reaction times, good yields of the products, and utilization of aspirin as a non-toxic, cheap, commercially available, and efficient catalyst.
- Fatahpour, Maryam,Noori Sadeh, Fatemeh,Hazeri, Nourallah,Maghsoodlou, Malek Taher,Lashkari, Mojtaba
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p. 1945 - 1956
(2017/08/14)
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- Synthesis of functionalized chromene and spirochromenes using L-proline-melamine as highly efficient and recyclable homogeneous catalyst at room temperature
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An efficient and recyclable homogeneous catalyst is developed using commercially cheap L-proline and melamine for the synthesis of chromenes and spirochromenes (spirooxindoles) via multicomponent reactions at room temperature. Systematic studies were conducted in order to achieve desired reactivity and recyclability of the catalyst using various α-amino acids and aromatic amines as donor-acceptor pairs. Among the screened combinations, L-proline and melamine (3:1 ratio; 3 mol% on total weight) was found to be best catalyst to give the desired products with excellent yields (up to 99%) in very short times (1–15 min) at room temperature in DMSO as solvent. The catalyst was recovered by adding EtOAc and reused up to 5 cycles without losing the catalytic activity.
- Nagaraju, Sakkani,Paplal, Banoth,Sathish, Kota,Giri, Santanab,Kashinath, Dhurke
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supporting information
p. 4200 - 4204
(2017/10/06)
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- One-pot multicomponent reaction synthesis of spirooxindoles promoted by guanidine-functionalized magnetic Fe3O4 nanoparticles
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Magnetic nanoparticles of Fe3O4-immobilized guanidine (MNPs-guanidine) have been characterized by powder X-ray diffraction (XRD), a vibrating sample magnetometer (VSM), scanning electronic microscopy (SEM), energy dispersive X-ray (E
- Tameh, Fatemeh Alemi,Safaei-Ghomi, Javad,Mahmoudi-Hashemi, Mohammad,Shahbazi-Alavi, Hossein
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p. 74802 - 74811
(2016/08/24)
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- Green synthesis of tetrahydrobenzo[b] pyrans, pyrano[2,3-c] pyrazoles and spiro[indoline-3,4′-pyrano[2,3-c] pyrazoles catalyzed by nano-structured diphosphate in water
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A green and recoverable nano-structured diphosphate (Na2CaP2O7) was synthesized and fully characterized using FT-IR spectra, X-ray diffraction patterns (XRD), scanning electron microscopy (SEM), and energy-dispersive X-ray
- Maleki, Behrooz,Nasiri, Negar,Tayebee, Reza,Khojastehnezhad, Amir,Akhlaghi, Hossien Ali
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p. 79128 - 79134
(2016/09/09)
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- Bovine serum albumin catalyzed one-pot, three-component synthesis of dihydropyrano[2,3-c]pyrazole derivatives in aqueous ethanol
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Bovine serum albumin (BSA) catalyzed synthesis of dihydropyrano[2,3-c]pyrazole derivatives via a one pot, three component reaction of an aldehyde/ketone/isatin, malononitrile and 3-methyl-1H-pyrazol-5-(4H)-one in H2O-EtOH (7: 3) at ambient temp
- Dalal, Kiran S.,Tayade, Yogesh A.,Wagh, Yogesh B.,Trivedi, Darshak R.,Dalal, Dipak S.,Chaudhari, Bhushan L.
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p. 14868 - 14879
(2016/02/19)
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- Green one-pot, four-component synthesis of spiro[indoline-3,4'-pyrano[2,3-c]pyrazole] derivatives using amino-functionalized nanoporous silica SBA-15 under solvent-free conditions
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Propylamine functionalized nanoporous silica (SBA-Pr-NH2) was used as an efficient heterogeneous solid basic nanoreactor in the synthesis of 6'-amino-1'H-spiro[indoline-3,4'-pyrano[2,3-c]pyrazol]-2-one derivatives 5 through a one-pot, four-comp
- Ziarani, Ghodsi Mohammadi,Rahimifard, Mahshid,Nouri, Fatemeh,Badiei, Alireza
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p. 1265 - 1272
(2016/02/18)
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- ZrO2 nanoparticles as a reusable solid dual acid-base catalyst for facile one-pot synthesis of multi-functionalized spirooxindole derivatives under solvent free condition
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A two-step one-pot protocol for the facile synthesis of biologically important spirooxindole derivatives such as spiro[4H-pyran-3,3′-oxindoles] and spiro[indoline-3,4′(1H′)-pyrano-[2,3-c]pyrazol-2-ones has been developed. In this method ZrO2 na
- Bodhak, Chandan,Kundu, Ashis,Pramanik, Animesh
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p. 85202 - 85213
(2015/11/02)
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- Chitosan/ionic liquid forms a renewable and reusable catalyst system used for the synthesis of highly functionalized spiro derivatives
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Chitosan, a reusable heterogeneous catalyst, can be combined with an ionic liquid as a green solvent to generate a highly efficient catalyst system for our densely functionalised and diversified target molecule. The reaction is completed with a good to ex
- Rai, Pratibha,Srivastava, Madhulika,Singh, Jagdamba,Singh, Jaya
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p. 3181 - 3186
(2014/07/07)
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- Green access to multi-component synthesis of spiropyranopyrazoles
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A catalyst-free multi-component synthesis of spiro[indoline-3,4'-pyrano[2, 3-c]pyrazoles] is reported from in situ formed pyrazolone by exothermic reaction of ethyl acetoacetate with hydrazine hydrate, isatin and malononitrile in water at room temperature. A suggested mechanistic approach was supported by semi-empirical calculations. The transformation is carried out in water alone and thus achieved the highest level of green chemistry. Simple reaction conditions, easy work-up procedure and isolation of products are the auxiliary advantages of present protocol.
- Pore,Hegade,Gaikwad,Patil,Patil
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p. 131 - 135
(2014/03/21)
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- Novel and efficient one-pot synthesis of spiro[indoline-3,4'-pyrano [2,3-c]pyrazole]derivatives catalysed by L-proline in aqueous medium
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An efficient mild one-pot synthesis of spiro[indoline-3,4'-pyrano[2,3-c] pyrazole derivatives by a four-component reaction of hydrazine, a β-keto ester, isatin, and malononitrile catalysed by L-proline in water is reported.
- Yu, Jiangxia,Zhou, Yongbing,Shen, Tianhua,Mao, Wengang,Chen, Kang,Song, Qingbao
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p. 365 - 368
(2013/07/26)
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- Ethylenediammonium diformate (EDDF) in PEG600: An efficient ambiphilic novel catalytic system for the one-pot synthesis of 4H-pyrans via Knoevenagel condensation
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A novel ethylenediammonium diformate-polyethylene glycol (EDDF-PEG 600) system was developed as a catalyst for the Knoevenagel condensation and Knoevenagel initiated three-component one-pot synthesis of 4H-pyrans at room temperature with high yields and in short reaction times. Further, the EDDF-PEG600 catalytic system was recycled six times without any appreciable loss in its activity and hence can be termed as a green, environmentally benign catalytic system. A plausible mechanism depicting the ambiphilic nature of EDDF (catalyst) and PEG (promoting medium) acting in synergy has been proposed. The Royal Society of Chemistry.
- Thakur, Anuj,Tripathi, Mohit,Rajesh, U. Chinna,Rawat, Diwan S.
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p. 18142 - 18148
(2013/10/01)
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- Rapid and efficient ultrasound-assisted method for the combinatorial synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] derivatives
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An efficient one-pot synthesis of spiro[indoline-3,4′-pyrano[2,3-c] pyrazole] derivatives by four-component reaction of hydrazine, β-keto ester, isatin, and malononitrile or ethyl cyanoacetate catalyzed by piperidine under ultrasound irradiation is descri
- Zou, Yi,Hu, Yu,Liu, Hai,Shi, Daqing
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experimental part
p. 38 - 43
(2012/02/05)
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- Solvent-free one-pot synthesis of spiro[indoline-3,4′(1h′)- pyrano-[2,3-c]pyrazol]-2-one derivatives by grinding
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The solvent-free one pot synthesis of spiropyranyl-oxindole in the presence of NaHCO3 under grinding has been achieved. This process is simple, fast, efficient and environmentally benign. Copyright Taylor & Francis Group, LLC.
- Liu, Ying,Ren, Zhongjiao,Cao, Weiguo,Chen, Jie,Deng, Hongmei,Shao, Min
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experimental part
p. 3620 - 3626
(2011/10/09)
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- A green efficient synthesis of spiro[indoline-3,4'(1H')-pyrano [2,3-c]pyrazol]-2-one derivatives
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A highly efficient and green method has been described for the synthesis of spiropyranopyrazole-oxindole in water. The reaction was carried out at ambient temperature and the products were obtained in excellent isolated yields. The structure of the produc
- Liua, Ying,Zhoua, Dong,Rena, Zhongjiao,Caoab, Weiguo,Chena, Jie,Dengc, Hongmei,Gua, Qing
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experimental part
p. 154 - 156
(2009/10/15)
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- Nitriles in Heterocyclic Synthesis. A Novel Synthesis of Spiropyran-4-Ylindolidene Derivatives
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The structure of the products of reaction of 2-oxo-3-dicyanomethylidene-2,3-dihydroindole (1a) and 2-oxo-3-cyanoethoxycarbonylmethylidene-2,3-dihydroindole (1b) with the pyrazolin-5-one derivatives 2a,b could be established via 13C nmr and high resolution
- Hafez, Ebtisam Abdel Aziz,Galil, Fathy M. Abdul,Sherif, Sherif M.,Elnagdi, Mohamed H.
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p. 1375 - 1378
(2007/10/02)
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