125418-83-9Relevant articles and documents
Multicomponent synthesis of substituted and fused-ring imidazoles via phospha-münchnone cycloaddition
Aly, Sara,Romashko, Mikhail,Arndtsen, Bruce A.
, p. 2709 - 2714 (2015)
A new, one-pot synthesis of imidazoles from imines, acid chlorides, and N-nosyl imines or tethered nitriles is reported. The reaction is mediated by the phosphonite PPh(catechyl) and proceeds via regioselective cycloaddition with an in situ-generated phos
Regioselective Synthesis of Benzo[h][1,6]-naphthyridines and Chromenopyrazinones through Alkyne Cyclization
Hoplamaz, Emre,Keskin, Selbi,Balci, Metin
, p. 1489 - 1497 (2017)
A regioselective approach to the synthesis of benzo[h][1,6]-naphthyridine and chromenopyrazinone derivatives was developed. The synthetic route to benzo[h][1,6]-naphthyridines involves the N-propargylation of aromatic aminobenzaldehydes, followed by reaction with propargylamine in the presence of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene). For the synthesis of chromenopyrazine and chromenopyrazinone derivatives, the acetonitrile group was introduced to salicylaldehyde derivatives, and a DBU-promoted cyclization reaction between aldehydes and propargylamine gave the chromenopyrazines. The intramolecular heterocycloaddition reaction between the triple bond and the azadiene, which is formed as an intermediate, gave the desired structures.
Gold/Lewis acid catalyzed oxidative cyclization involving activation of nitriles
Wang, Ali,Xie, Xin,Zhang, Chunli,Liu, Yuanhong
supporting information, p. 15581 - 15584 (2020/12/30)
A gold-catalyzed oxidative cyclization of alkyne-nitriles using water or alcohol as the external nucleophiles has been developed. The catalytic system, featured with gold and Lewis acid dual catalysis, allows a facile synthesis of functionalized isoquinolin-1(2H)-ones and 1-alkoxy-isoquinolines with a wide structural diversity. This journal is
NHC-catalyzed green synthesis of functionalized chromones: DFT mechanistic insights and: In vitro activities in cancer cells
Murugesh, Nithya,Haribabu, Jebiti,Arumugam, Krishnamoorthy,Balachandran, Chandrasekar,Swaathy, Rajagopal,Aoki, Shin,Sreekanth, Anandaram,Karvembu, Ramasamy,Vedachalam, Seenuvasan
supporting information, p. 13509 - 13525 (2019/09/06)
An efficient synthesis of 3-aminochromones and 3-alkylchromones by a N-heterocyclic carbene (NHC) catalyzed intramolecular hydroacylation reaction of corresponding salicylaldehyde derived nitriles and activated alkynes respectively in ionic liquids under microwave conditions is reported. This protocol has the advantages of environmental friendliness, higher yields, shorter reaction times, and convenient operation using the commercially available thiazolium catalyst. The origin of the chemical reactivity of the NHC-catalyzed intramolecular hydroacylation reaction of nitriles is studied using Density Functional Theory (DFT). The results suggest that 3-aminochromone formation occurs via an acyl anion intermediate called a Breslow intermediate (INT2) through TS2. The Breslow intermediate (INT2) forms a carbon-carbon bond with the nitrile carbon to produce an imine intermediate INT3viaTS3, which further undergoes imine to amine tautomerism to give the end product. Some of the derivatives of 3-aminochromone are subjected to amine functionalization in one pot to obtain a library of compounds for anticancer activity. Among the investigated compounds, 2c (SVM-2), 4c (SVM-4) and 2d (SVM-9) show IC50 values of 5.18, 4.89 and 27.3 μM respectively in HeLa S3 cancer cells. Compound 5c (SVM-5) shows IC50 values of 13.3 and 14.2 μM in A549 and HeLa S3 cancer cells, respectively. Compounds 2c (SVM-2) and 4c (SVM-4) produce morphological changes and control the colony formation in HeLa S3 cells, which indicates that these small molecules are potential candidates for anticancer drugs.
A step-economical route to fused 1,2,3-triazoles via an intramolecular 1,3-dipolar cycloaddition between a nitrile and an in situ generated aryldiazomethane
Mani, Neelakandha S.,Fitzgerald, Anne E.
, p. 8889 - 8894 (2015/01/08)
An intramolecular 1,3-dipolar cycloaddition strategy for rapid entry into triazole-fused heterocyclic compounds without recourse to the traditional Cu(1)-catalyzed azide-alkyne cycloadditions is described. Central to the strategy is the in situ generation of substituted diazomethanes in a two-step sequence from the corresponding aldehydes, which then undergo smooth cycloaddition with a cyano group to generate the desired fused 1,2,3-triazoles in good overall yields. The entire sequence can be carried out in a onepot operation.
Iridium-catalyzed hydrogen transfer: Synthesis of substituted benzofurans, benzothiophenes, and indoles from benzyl alcohols
Anxionnat, Bruno,Gomez Pardo, Domingo,Ricci, Gino,Rossen, Kai,Cossy, Janine
supporting information, p. 3876 - 3879 (2013/09/02)
An iridium-catalyzed hydrogen transfer has been developed in the presence of p-benzoquinone, allowing the synthesis of a diversity of substituted benzofurans, benzothiophenes, and indoles from substituted benzylic alcohols.
N-heterocyclic carbene-catalyzed intramolecular aldehyde-nitrile cross coupling: An easy access to 3-aminochromones
Vedachalam, Seenuvasan,Zeng, Jing,Gorityala, Bala Kishan,Antonio, Meraldo,Liu, Xue-Wel
supporting information; experimental part, p. 352 - 355 (2010/03/24)
(Figure presented) An immense effort has been made to develop an efficient strategy for the carbon-carbon bond formation between aldehyde and nitrile intramolecularly using an N-heterocyclic carbene catalyst to derive 3-aminochromone derivatives In good to excellent yields (80-95%).
Amine compounds, their production and use
-
, (2008/06/13)
The present invention provides a compound of the formula: wherein Ar represents an aromatic group which may be substituted; X represents methylene, S, SO, SO2or CO; Y represents a spacer having a main chain of 2 to 5 atoms; n represents an integer of 1 to 5; i) R1and R2each represents a hydrogen atom or a lower alkyl which may be substituted, ii) R1and R2form, taken together with the adjacent nitrogen atom, a nitrogen-containing heterocyclic ring which may be substituted, or iii) R1or R2together with —(CH2)n—N═ form, bonded to a component atom of Ring B, a spiro-ring which may be substituted; Ring A represents an aromatic ring which may be substituted; Ring B represents a 4- to 7-membered nitrogen-containing non-aromatic ring which may be further substituted by alkyl or acyl, with a proviso that X represents S, SO, SO2or CO when Ring A has as a substituent a group represented by the formula: —NHCOR11 where R11represents alkyl, alkoxyalkyl, alkylthioalkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or a group represented by the formula: —NHR12 where R12represents alkyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, or a salt thereof; which has an excellent somatostatin receptor binding inhibition action.