13324-83-9Relevant academic research and scientific papers
Potassium tert-Butoxide Promoted Synthesis of Dihydroquinazolinones
Basak, Soumya Jyoti,Dash, Jyotirmayee,Ghosh, Tridev,Mandal, Indradip
supporting information, p. 14695 - 14704 (2021/10/20)
We herein report an efficient synthetic protocol to access heterocyclic dihydroquinazolinones by a transition-metal-free process, involving the reaction of 2-aminobenzonitriles with aldehydes in the presence of KOtBu. The method is compatible with aromatic ketones providing 2,2-disubstituted dihydroquinazolinones in high yields. This reaction proceeds feasibly at room temperature and features a broad substrate scope and tolerance to a range of functional groups. The mechanism follows a radical pathway.
β-Cyclodextrin: A supramolecular catalyst for metal-free approach towards the synthesis of 2-amino-4,6-diphenylnicotinonitriles and 2,3-dihydroquinazolin-4(1 H)-one
Mitra, Bijeta,Chandra Pariyar, Gyan,Ghosh, Pranab
, p. 1271 - 1281 (2021/01/20)
β-Cyclodextrin, a green and widespread supramolecular catalyst, has been explored as a highly proficient promoter for the metal-free one-pot multi-component synthesis of a vast range of highly functionalized bioactive heterocyclic moiety, 2-amino-4,6-diphenylnicotinonitriles and 2,3-dihydroquinazolin-4(1H)-one, from easily available precursor aldehydes. The main endeavor of these protocols is to explore this organic supramolecule in one-pot multi-component synthesis. Absence of metal catalyst or toxic acid and harsh reaction conditions, excellent functional group tolerance, inexpensive, greener and environmentally safe protocol are the key advantages of this work.
Sustainable parts-per-million level catalysis with FeIII: One-pot cascade synthesis of 2,3-dihydroquinazolin-4(1H)-ones in water
Dutta, Apurba,Trivedi, Priyanka,Kulshrestha, Akshay,Kumar, Arvind,Chaturvedi, Vinita,Sarma, Diganta
, (2020/12/13)
A silica-supported iron complex has been identified as a highly active and reusable catalyst for the synthesis of medicinally important 2,3-dihydroquinazolin-4(1H)-ones. The catalyst was fully characterized by various spectroscopic analyses such as Fourie
The novel acid-base magnetic recyclable catalyst prepared through carbon disulfide trapping process: Applied for green, one-pot, and efficient synthesis of 2,3-dihydroquinazolin-4 (1H) -ones and bis(indolyl)methanes in large-scale
Mohammadi Metkazini, Fatemeh,Khorsandi, Zahra,Heydari, Akbar
, (2021/04/12)
Herein, a nano acid-base catalyst using magnetic core and carbamodithioic acid functional group have been synthesized and characterized. Its efficiency in the synthesis of dihydroquinazolinones and bis(indolyl)methanes derivatives was investigated. This novel metal-free catalyst exhibited significant catalytic activity in both reactions under green and mild reaction conditions (the yield obtained for the first reaction products: 82–98 % and for the second one: 61–97 %). The catalyst displayed good recyclability with no significant loss of catalytic activity after eight runs (the conversion of the eighth run was found as 83 %, the fresh catalyst conversion was 95 %). The introduced approach is attractive due to its applicability in the large-scale synthesis of important medicinal compounds.
Probing the catalytic activity of highly efficient sulfonic acid fabricated cobalt ferrite magnetic nanoparticles for the clean and scalable synthesis of dihydro, spiro and bis quinazolinones
Awasthi, Satish K.,Yadav, Priyanka
supporting information, p. 15928 - 15941 (2021/09/22)
An exceptionally productive, rapid, simple, and eco-friendly approach for the synthesis of 2,3-dihydroquinazolin-4(1H)-one has been developed utilizing acidic magnetically retrievable cobalt ferrite nanoparticles (CFNP@SO3H). Herein, we have demonstrated the synthesis of these profoundly demanding N-heterocyclic molecules within 3-10 min in excellent yields at room temperature using the environmentally benign solvent ethanol. Outstanding catalytic performance, ease of retrievability, high turnover frequency (TOF) values (197.13-403.23 h?1), admirable green chemistry metrices, such as theEfactor (0.10), reaction mass efficiency (RME) value (90.9%), carbon efficiency (100%) and atom economy (AE) value (92.6%), and reusability for up to six runs without a significant loss of activity, make the current methodology advantageous from an environmental, as well as industrial perspective.
One-Pot, Borax-mediated synthesis of structurally diverse N, S-heterocycles in water
Rao, Mugada Sugunakara,Hussain, Sahid
, (2021/05/26)
Herein, a borax–mediated convenient and efficient strategy for the synthesis of prominent structurally diverse N, S-heterocycles such as quinazolin-4(3H)-one, benzothiadiazine 1,1-dioxide, benzothioazole, and benzoxazoles from readily available 2-aminobenzamide/2-aminobenzenesulfonamide/2-aminothiophenol/2-aminophenol with α,α,α-trihalotoluenes at 100 ℃ in water is elaborated. Upon using aldehydes instead of α,α,α-trihalotoluenes, the reactions proceed through domino fashion under the catalytic effect borax to yield 2,3-dihydroquinazolin-4(1H)-one, 3,4-dihydrothiadiazine 1,1-dioxide, and benzothiazoles in one-pot at 60 ℃. The advantages of this protocol are practical simplicity, large substrate scope, moderate to excellent yields, and the use of water as the solvent.
The Rh(iii)-catalysed C-H/N-H annulation of 2-thienyl- And 2-phenyl-quinazolin-4(3: H)-ones with diphenylacetylene
Moshkina, Tatyana N.,Nosova, Emiliya V.,Lipunova, Galina N.,Zhilina, Ekaterina F.,Slepukhin, Pavel A.,Nikonov, Igor L.,Charushin, Valery N.
, p. 8456 - 8466 (2021/05/26)
A series of 4,5-diphenyl-7H-thieno[2′,3′:3,4]pyrido[2,1-b]quinazolin-7-ones was synthesized via the Rh(iii)-catalyzed annulation of 2-thienylquinazolin-4(3H)-ones with diphenylacetylene. 2-Phenylquinazolin-4(3H)-one amide alcoholysis and double C-H functionalization proceeded under the same reaction conditions with the formation of 2,3,7,8-tetraphenyl-1H-benzo[d,e][1,8]-naphthyridine derivatives. All compounds possess fluorescence properties in MeCN and toluene solutions as well as in the solid state. The aggregation induced emission (AIE) properties and the ability to detect Fe3+ cations were evaluated.
Glucose as an Eco-Friendly Reductant in a One-Pot Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones
dos Santos, Thiago,Grundke, Caroline,Lucas, Tobias,Gro?mann, Luca,Clososki, Giuliano Cesar,Opatz, Till
supporting information, p. 6429 - 6432 (2020/09/02)
Carbohydrates such as glucose are an abundant renewable resource that can be employed in synthetic processes as a source of carbon and/or hydrogen to yield products of high economical and biological impact. Herein, we report a versatile and environmentally friendly protocol for the one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones, a privileged scaffold in medicinal chemistry, based on the use of glucose as an eco-friendly reductant in alkaline aqueous medium. This method can be viewed as a blueprint for the development of further one-pot sequences involving glucose as a reductant.
Gemini basic ionic liquid as bi-functional catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones at room temperature
Dutta, Apurba,Damarla, Krishnaiah,Kumar, Arvind,Saikia, Prakash J.,Sarma, Diganta
, (2020/01/08)
A cascade synthesis of 2,3-dihydroquinazolin-4(1H)-ones has been developed from 2-aminobenzonitriles and carbonyl analogues using Gemini basic ionic liquid as green catalyst cum solvent at room temperature. Both aldehydes and ketones were condensed with 2-aminobenzonitriles affording good to excellent yields of products. Moreover, the ionic liquids can be reused up to 5th cycle without significant loss of catalytic activity.
An expeditious synthesis of 2,3-dihydroquinozoline-4(1H)-ones using graphene-supported sulfonic acid
Gajare, Shivanand,Jagadale, Megha,Naikwade, Altafhusen,Bansode, Prakash,Patil, Pradnya,Rashinkar, Gajanan
, p. 89 - 102 (2019/12/24)
Graphene-supported sulfonic acid (Gr?SO3H) has been prepared by covalent grafting of (3-mercaptopropyl)trimethoxysilane in the matrix of graphene followed by treatment with sulfuric acid and hydrogen peroxide. Gr?SO3H has been successfully characterized by Fourier transform infrared (FT-IR) spectroscopy, Fourier transform Raman (FT-Raman) spectroscopy, CP-MAS 13C NMR spectroscopy, thermogravimetric analysis (TGA), energy dispersive X-ray analysis (EDX), transmission electron microscopy (TEM), Brunauer-Emmett-Teller (BET) analysis, and X-ray diffractometer (XRD) analysis. Gr?SO3H served as a robust heterogeneous catalyst for the synthesis of bioactive 2,3-dihydroquinazolin-4(1H)-ones from anthranilamide and aryl aldehydes in ethanol. Recyclability experiments were executed successfully for six consecutive runs.
