- Organocatalytic Cascade Knoevenagel–Michael Addition Reactions: Direct Synthesis of Polysubstituted 2-Amino-4H-Chromene Derivatives
-
Abstract: In this report, we documented novel strategy for the synthesis of bioactive polysubstituted 2-amino-4H-chromine derivatives under a heterogeneous Al-MCM-41-LDH@APTES (ALAM) catalysis. A synthetic procedure is developed to prepare Al-MCM-41-LDH@APTES (ALAM) heterogeneous basic catalysts. Mesoporous Al-MCM-41 is functionalized by known grafting chemistry via layered double hydroxide (LDH) nanosheets and (3-aminopropyl)triethoxysilane (APTES) moiety as a basic organocatalyst. The resulting catalysts contain amino group functionality on the external surface as well as inside the layers and the basicity can be tuned by the loading of APTES. The samples were fully characterized by 29Si and 13C CP/MAS NMR, infrared absorption spectroscopy, TEM, XPS, EDX, TGA, XRD, CO2-TPD, N2 adsorption isotherms measurements, and they were successfully examined for the cascade type Knoevenagel–Michael addition reactions. The product yields associated with these substrates were optimized, and key reaction parameters affecting the yields were identified. The present catalytic method is simple and robust for diversity oriented synthesis which proceeds good to excellent yields without generating any hazards waste. The broad substrate scope, excellent functional group compatibility makes this protocol highly useful towards synthesis of polysubstituted α-cyanoacrylates, α-cyanoacrylonitriles and 2-amino-4H-chromenes with an electron-donating or electron-withdrawing group. We have also successfully established a flow reaction system, gram-scale synthesis as well as catalyst recyclability up to six catalytic cycles without appreciable loss of its activity. Graphic Abstract: [Figure not available: see fulltext.].
- Jadhav, Sanjay N.,Patil, Seema P.,Sahoo, Dipti Prava,Rath, Dharitri,Parida, Kulamani,Rode, Chandrashekhar V.
-
p. 2331 - 2351
(2020/02/25)
-
- A green method synthesis and antimicrobial activity of 2-amino-4H-chromene derivatives
-
Agro-waste stuff ash extracted solution have been emerging in recent practicing green reaction catalysis in organic synthesis. The derived media have been demonstrated in reactions like Sonogashira, Dakin, Henry, Suzuki-Miyaura, amide bond formation. Trad
- Kantharaju,Khatavi, Santosh Y.
-
p. 1496 - 1502
(2018/06/12)
-
- Synthesis, screening and docking of fused pyrano[3,2-d]pyrimidine derivatives as xanthine oxidase inhibitor
-
In view of developing effective xanthine oxidase (XO) enzyme inhibitors, a series of 100 pyrano[3,2-d]pyrimidine derivatives was synthesized and evaluated for its in vitro XO enzyme inhibition. Structure activity relationship has also been established. Am
- Kaur, Manroopraj,Kaur, Amandeep,Mankotia, Suhani,Singh, Harbinder,Singh, Arshdeep,Singh, Jatinder Vir,Gupta, Manish Kumar,Sharma, Sahil,Nepali, Kunal,Bedi, Preet Mohinder Singh
-
-
- Diisopropyl azodicarboxylate mediated selective dehydrogenation of 2-amino-3-cyano 4H-chromenes
-
Selective dehydrogenation of 2-amino-3-cyano 4H-chromenes to the corresponding 2-iminochromenes mediated by diisopropyl azodicarboxylate under neutral conditions is reported. The dehydrogenation reaction is compatible with phenolic hydroxyl group and gene
- Sharma, Himanshu,Mourya, Mohini,Guin, Debanjan,Joshi, Yogesh C.,Dobhal, Mahabeer P.,Basak, Ashok K.
-
p. 1727 - 1732
(2017/04/13)
-
- Synthesis, characterization, anti-bacterial, anti-fungal and nematicidal activities of 2-amino-3-cyanochromenes
-
Soil-borne plant pathogens such as nematodes, fungi and some bacteria not only affect the plant cultures but also economy and environmental implications. As a result of these pathogens attacks, the yield and quality of crops is affected. Therefore, synthe
- Nawaz, Muhammad,Abbasi, Muhammad Waseem,Hisaindee, Soleiman
-
p. 160 - 163
(2016/10/03)
-
- Iodine mediated synthesis of coumarins from chromenes
-
Iodine mediated rapid conversion of 2-amino-3-cyano-4-aryl-4H chromenes to the corresponding coumarins in the presence of water is described. Several chromenes are obtained in high yields without chromatographic purification. Under anhydrous conditions, 2
- Sharma, Himanshu,Mourya, Mohini,Soni, Lokesh K.,Guin, Debanjan,Joshi, Yogesh C.,Dobhal, Mahaveer P.,Basak, Ashok K.
-
p. 7100 - 7104
(2015/12/01)
-
- Screening of a library of 4-aryl/heteroaryl-4H-fused pyrans for xanthine oxidase inhibition: Synthesis, biological evaluation and docking studies
-
A series of 4-aryl/heteroaryl-4H-fused pyrans was synthesized via multicomponent reaction in a microwave synthesizer. All the pyrans were evaluated for in vitro xanthine oxidase inhibition. Structure-activity relationship was also established. Among the s
- Kaur, Ramandeep,Naaz, Fatima,Sharma, Sahil,Mehndiratta, Samir,Gupta, Manish Kumar,Bedi, Preet Mohinder Singh,Nepali, Kunal
-
p. 3334 - 3349
(2015/08/03)
-
- Heterogeneous ditopic ZnFe2O4 catalyzed synthesis of 4H-pyrans: Further conversion to 1,4-DHPs and report of functional group interconversion from amide to ester
-
Highly stable, environmentally benign ZnFe2O4 nanopowder was prepared, characterized and applied in the one-pot, three-component synthesis of 4H-pyrans in water. The ZnFe2O 4 catalyst provides both acidic (Fesu
- Das, Paramita,Dutta, Arghya,Bhaumik, Asim,Mukhopadhyay, Chhanda
-
p. 1426 - 1435
(2014/03/21)
-
- On water CuSO4. 5H2O-catalyzed synthesis of 2-amino-4H-chromenes
-
Sustainable development is a balance between environment and development. Sustainable development requires sustainable supplies of clean, affordable, and renewable energy sources that do not cause negative impact to the society. This article introduces a
- Behbahani, Farahnaz Kargar,Maryam, Sadeghi
-
p. 357 - 360
(2013/07/26)
-
- Highly efficient conversion of fused 2-amino-4-aryl-4H-chromene-3- carbonitriles into fused 2-oxo-4-aryl-2H-chromene-3-carbonitriles using Vilsmeier conditions
-
A simple, mild, and highly efficient protocol for the synthesis of fused 2-oxo-4-aryl-2H-chromene-3-carbonitriles has been developed starting from fused 2-amino-4-aryl-4H-chromene-3-carbonitriles utilizing Vilsmeier conditions.
- Banothu, Janardhan,Velpula, Ravibabu,Gali, Rajitha,Bavantula, Rajitha,Crooks, Peter A.
-
p. 3862 - 3864
(2013/07/05)
-
- Efficient and eco-friendly synthesis of 2-amino-4H-chromene derivatives using catalytic amount of tetrabutylammonium chloride (TBAC) in water and solvent-free conditions
-
A simple, efficient and eco-friendly procedure has been developed using tetrabutylammonium chloride as catalyst for the synthesis of 2-amino-4H-chromene derivatives in water and solvent-free neat conditions. The present methodology offers several advantag
- Mehrabi, Hossein,Kamali, Nafiseh
-
p. 599 - 605
(2013/02/22)
-
- Basic magnetic nanoparticles as efficient catalysts for the preparation of naphthopyrane derivatives
-
Aminosilane-functionalised spinel ferrite oxide (Fe2O 3 ) magnetic nanoparticles have been synthesised and used as efficient heterogeneous base catalysts for the condensation of aromatic aldehydes with malonitrile and α (or β) naphth
- Yarahmadi, Hossein,Shaterian, Hamid Reza
-
experimental part
p. 49 - 51
(2012/04/04)
-
- Disodium hydrogen phosphate as an efficient and cheap catalyst for the synthesis of 2-aminochromenes
-
An efficient and convenient method for the synthesis of 2-aminochromene by the one-pot, three-component reaction of an aromatic aldehyde, malononitrile, and-or-naphthol in the presence of a catalytic amount of disodium hydrogen phosphate under solvent-fre
- Meng, Xin-Ying,Wang, Hong-Juan,Wang, Chun-Ping,Zhang, Zhan-Hui
-
experimental part
p. 3477 - 3484
(2011/09/16)
-
- DBU: A highly efficient catalyst for one-pot synthesis of substituted 3, 4- dihydropyrano[3, 2-c]chromenes, dihydropyrano[4, 3-b]pyranes, 2-amino-4H- benzo[h]chromenes and 2-amino-4H benzo[g]chromenes in aqueous medium
-
We have reported DBU catalyzed one-pot synthesis of 3, 4-dihydropyrano[3, 2-c]chromenes, dihy- dropyrano[4, 3-b]pyranes, 2-amino-4H-benzo[h]chromenes and 2-amino-4H-benzo[g]chromenes from aldehydes, active methylene compounds malononitrile/ethyl cyanocace
- Khurana, Jitender M.,Nand, Bhaskara,Saluja, Pooja
-
experimental part
p. 5637 - 5641
(2010/09/18)
-
- Aliquat 336 catalysed three-component condensation in an aqueous media: A synthesis of 1H- and 4H-benzochromenes
-
The synthesis, under microwave irradiation, of a series of polyfunctionalised 1H- and AH- chromenes in water in the presence of tricaprylmethylammonium bromide (Aliquat 336) as the catalyst is reported. This method has the advantages of high yields, neutr
- Patra, Amarendra,Mahapatra, Tanusri
-
experimental part
p. 405 - 408
(2009/11/30)
-
- Synthesis of 2-Aminochromene Derivatives Catalyzed by KF/Al 203
-
A series of 2-aminochromene derivatives include 2-aminobenzo-[h]chromene, and naphtha[1,2-b;6,5-b′]dipyrans derivatives were synthesized from arylaldehyde, malononitrile or ethyl cyanoacetate with 1-naphthol or 1,5-naphthalenediol in refluxing ethyl alcohol catalyzed by KF-A1 203. The structure of the products was confirmed by X-ray analysis.
- Wang, Xiang-Shan,Shi, Da-Qing,Yu, Hui-Zhen,Wang, Gao-Feng,Tu, Shu-Jiang
-
p. 509 - 514
(2007/10/03)
-
- Pharmaceutical compounds
-
The invention provides pharmaceutical compounds of the formula: STR1 in which A - - - B is CH2 --CH2 or CH=CH; X is a pyridine or benzene ring; when X is pyridine n is 0; when X is benzene n is 0, 1 or 2 and when A - - - B is CH
- -
-
-
- Therapy for diabetic complications
-
This invention provides a method of treating diabetic complications in mammals which comprises the administration of a compound of the Formula I: STR1 in which n, R1, R2, R3, and R4 are variables.
- -
-
-