13623-98-8Relevant articles and documents
Microwave-assisted synthesis of n-heterocycles and their evaluation using an acetylcholinesterase immobilized capillary reactor
Sangi, Diego P.,Monteiro, Julia L.,Vanzolini, Kenia L.,Cass, Quezia B.,Paixa?o, Marcio W.,Corre?a, Arlene G.
, p. 887 - 889 (2014)
Polarized ketene dithioketals have been recognized as useful building blocks in many synthetic operations. In this work, a transition-metal-free annulations of 1,1-bis(thiomethyl)-2-nitroethylene with hydroxylalkylamines or alkyldiamines have been reported. This methodology provides a directed approach to N-heterocycles, e.g., imidazolidines, oxazolidines and benzoxazoles under microwave conditions. These compounds were evaluated as acetylcholinesterase inhibitors by using an enzyme immobilized capillary reactor-tandem mass spectrometry.
Efficient synthesis of chromenopyridines containing intramolecular hydrogen bonds through a sequential three-component reaction
Alizadeh, Abdolali,Bayat, Fahimeh,Zhu, Zhe
, p. 5927 - 5936 (2016)
A one-pot sequential reaction of 1,1-bis(methylsulfanyl)-2-nitroethene, diamines, and 3‐formylchromones in EtOH has been developed to afford chromenopyridines. The method is operationally simple and the products are obtained in good yields.
Simple synthesis of new imidazopyridinone, pyridopyrimidinone, and thiazolopyridinone derivatives and optimization of reaction parameters using response surface methodology
Hosseini, Fahimeh Sadat,Bayat, Mohammad
, p. 30479 - 30488 (2019)
The reaction between ketene animal/ketene N,S-acetals (derived from diamines/cysteamine hydrochloride and 1,1-bis(methylthio)-2-nitroethene) with aromatic aldehydes, and Meldrum's acid led to the title compounds. The reaction conditions were optimized using response surface methodology (RSM). The two independent variables (temperature and water content of aqueous ethanol), and the responses (yield of product and reaction time) were studied. The range of each parameter selected was: T = 25-100 °C and water = 0-100%. The optimal values were: T = 72 °C and water = 33%. This work offers significant advantages including use of a green solvent, experimental simplicity, absence of catalyst, a simple work-up and purification process, moderate to good yields, and preparation of potentially bioactive compounds.
Iodine catalyzed mild 4CR protocol for synthesis of Tetrahydroimidazo[1,2-a]pyridines: Cascade construction of multiple C-C and C-Hetero bonds
Rezvanian, Atieh
, p. 4752 - 4756 (2015)
A highly convergent and straight forward synthesis of N-fused heterocycles, including 1,2,3,7-tetrahydroimidazo[1,2-a]pyridine-5-carboxylic acids is successfully achieved via a one-pot four-component cascade reaction utilizing pyruvic acid, aldehydes, dia
Highly efficient, one-pot synthesis of novel bis-spirooxindoles with skeletal diversity: Via sequential multi-component reaction in PEG-400 as a biodegradable solvent
Safari, Ensieh,Maryamabadi, Ammar,Hasaninejad, Alireza
, p. 39502 - 39511 (2017)
A green and efficient one-pot, sequential, multi-component protocol has been developed for the synthesis of some novel symmetrical bis-spirooxindole derivatives from the reaction of isatins, dihalides, malono derivatives and C-H activated carbonyl compoun
An efficient synthesis of spiro-oxindole derivatives by three-component reactions in water
Alizadeh, Abdolali,Moafi, Leila
, p. 546 - 551 (2015)
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).
Efficient access to pyrido[1,2-a]pyrimidines and imidazo[1,2-a]pyridines through Knoevenagel reaction/aza–ene addition/intramolecular cyclization
Alizadeh, Abdolali,Roosta, Atefeh,Rezaiyehraad, Reza
, p. 1123 - 1130 (2020)
Abstract: An expeditious metal-free heteroannulation reaction for pyrido[1,2-a]pyrimidines/imidazo[1,2-a]pyridines was developed in green solvent under mild reaction conditions by using three-component reaction of 2-chloroquinoline-3-carbaldehyde, malononitrile and nitroketen aminals, which obtained from the reaction between 1,1-bis(methylthio)-2-nitroethylene and diamines in green solvent under EtOH reflux conditions. This one-pot strategy is very simple and occurs in two steps. The present sequence is visualized as an environmentally benign process with excellent purity and high yields. Graphic abstract: An efficient, useful and general procedure for the synthesis of pyrido[1,2-a]pyrimidines/imidazo[1,2-a]pyridines via a one-pot three-component reaction of 2-chloroquinoline-3-carbaldehyde, malononitrile/ethyl 2-cyanoacetate and nitroketen aminals under mild and catalyst-free conditions in excellent yields is described. The major advantages of this protocol are high yields, mild and catalyst-free conditions, short reaction times and application of green solvent.[Figure not available: see fulltext.].
An efficient synthesis of chromeno[2,3-d]pyrimidine-2,4-diones with a nitroketene-aminal moiety at C(5) by a one-pot four-component reaction
Alizadeh, Abdolali,Ghanbaripour, Rashid,Weng Ng, Seik
, p. 663 - 667 (2015)
Abstract An efficient and novel synthesis of chromeno[2,3-d]pyrimidine-2,4-dione derivatives with a nitroketene-aminal moiety at C(5) via four-component reaction of salicylaldehydes, barbituric acid, diamines, and 1,1-bis(methylsulfanyl)-2-nitroethene in EtOH and in the presence of AcOH is reported. Easy performance, good yields, and easy purification are the main advantages of this method. All structures were confirmed by IR, MS, and 1H- and 13C-NMR, and by X-ray crystal-structure analyses. A plausible mechanism for this type of reaction is proposed (Scheme).
Simple synthesis of benzo[g]imidazo[1,2-a]quinolinedione derivatives via a one-pot, four-component reaction
Bayat, Mohammad,Hosseini, Fahimeh,Notash, Behrouz
, p. 5439 - 5441 (2016)
The one-pot multicomponent synthesis of benzo[g]imidazo[1,2-a]quinolone-6,11-dione derivatives in good to high yields, from readily available starting materials including ethylenediamine, 1,1-bis(methylthio)-2-nitroethene, 2-hydroxy-1,4-naphthoquinone and
Synthesis of 1,2,3,5-substituted pyrroles from α-bromoacetophenones and 2-nitroethene-1,1-diamines
Mojikhalifeh, Sanaz,Hasaninejad, Alireza
, p. 2574 - 2577 (2017)
The simple synthesis of 1,2,3,5-substituted pyrroles from α-bromoacetophenones and 2-nitroethene-1,1-diamines in the presence of K2CO3 in DMF at 120?°C is described. A range of fused and non-fused polysubstituted pyrroles were prepared in high yields with short reaction times.
