222167-31-9Relevant academic research and scientific papers
Synthesis of 3,4-disubstituted isoquinolines via palladium-catalyzed cross-coupling of 2-(1-Alkynyl)benzaldimines and organic halides
Dai, Guangxiu,Larock, Richard C.
, p. 920 - 928 (2003)
The palladium-catalyzed cross-coupling of readily available N-tert-butyl-2-(1-alkynyl)benzaldimines and aryl, allylic, benzylic, alkynyl halides, as well as a vinylic halide, provides a valuable new route to 3,4-disubstituted isoquinolines with aryl, allylic, benzylic, 1-alkynyl, and vinylic substituents, respectively, in the 4-position. The reaction appears to require an aryl group on the end of the acetylene furthest from the imine functionality. The reaction conditions have been optimized, and reasonably good yields have been obtained.
Organic luminescent material based on 1, 6-naphthyridine receptor structural unit and application thereof
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Paragraph 0054-0056, (2021/01/12)
The invention discloses an organic luminescent material containing a 1, 6-naphthyridine receptor structural unit as shown in a formula (1) and application of the organic luminescent material. According to the organic luminescent material, the electrophilic 1, 6-naphthyridine structural unit is taken as a receptor, different donors are combined, a thermally induced delayed fluorescence material with high quantum efficiency, easily adjustable light-emitting color and good thermal stability can be formed, and can be used for preparing a dark blue light-emitting device and has a huge application prospect in the field of OLED materials.
One-pot Synthesis of Isoquinoline-Fused Isoquinolines via Intramolecular Hydroamination/Aza-Claisen Type Rearrangement Cascade
Chiu, Wei-Jung,Chen, Jin-Yu,Liu, Shih-I,Barve, Indrajeet J.,Huang, Wan-Wen,Sun, Chung-Ming
, p. 2834 - 2842 (2021/04/26)
A one-pot, two-step synthesis of isoquinoline-fused isoquinolines from α-amino acid esters and 2-alkynyl benzaldehydes are reported. The strategy comprises an unconventional Pictet-Spengler reaction between α-amino acid esters and 2-alkynyl benzaldehydes to give isoquinoline intermediates. Subsequent gold-catalyzed intramolecular hydroamination furnishes isoquinoline-fused isoquinolines. The scope of this strategy is further extended to prepare multisubstituted isoquinoline-fused isoquinolines via subjecting the N-allylated isoquinoline intermediates to gold-catalyzed intramolecular hydroamination followed by aza-Claisen type rearrangement. (Figure presented.).
Single Cu(I)-Photosensitizer Enabling Combination of Energy-Transfer and Photoredox Catalysis for the Synthesis of Benzo[ b]fluorenols from 1,6-Enynes
Zheng, Limeng,Xue, Han,Zhou, Bingwei,Luo, Shu-Ping,Jin, Hongwei,Liu, Yunkui
supporting information, p. 4478 - 4482 (2021/05/26)
An efficient, mild, and atom-economical synthesis of benzo[b]fluorenols from 1,6-enynes has been developed under photocatalytic conditions. A single P/N heteroleptic Cu(I)-photosensitizer might exhibit both energy-transfer and photoredox catalytic activities in the formation of benzo[b]fluorenols.
Transition-metal-free oxidative cyclization reaction of enynals to access pyrane-2-one derivatives
Abbasi Kejani, Alireza,Ansari, Farzaneh,Armaghan, Mahsa,Balalaie, Saeed,Frank, Walter,Jafarpour, Farnaz,Khosravi, Hormoz
supporting information, p. 4263 - 4267 (2021/05/31)
A novel and efficient metal-free C-H functionalization of enynals is developed to synthesize α-pyrone derivatives via the formation of two C-O bonds. In this project, K2S2O8 has been introduced as an efficient oxygen source and C-H functionalization agent in regioselective oxidative cyclization reaction with a relatively broad substrate scope.
Synthesis of cyclopentaquinolinone and cyclopentapyridinone from: Ortho-alkynyl-N-arylaldehyde via superbase-promoted C-N, C-O and C-C bond formation
Saini, Kapil Mohan,Saunthwal, Rakesh K.,Sushmita,Verma, Akhilesh K.
supporting information, p. 5594 - 5601 (2020/08/21)
An environmentally benign, transition metal-free, superbase-mediated intramolecular annulation of o-alkynylaldehydes with primary amines forms highly functionalized amino-substituted cyclopentaquinolinones and cyclopentapyridinones via C-N, C-C, and CO bond formation. Contrary to the traditional approaches of ring closures, a different mode of annulation is disclosed. The protocol involves the in situ generations of imine intermediate followed by potassium hydroxide-promoted intramolecular cyclization and subsequent dimethyl sulfoxide induced dehydrogenation leads to the formation of N-heterocycles. X-ray crystallographic studies support the assigned structures of the amino-fused N-heterocycles.
Catalytic asymmetric three-component reaction of 2-alkynylbenzaldehydes, amines, and dimethylphosphonate
Zou, Liangliang,Huang, Jiaying,Liao, Na,Liu, Yan,Guo, Qixiang,Peng, Yungui
supporting information, p. 6932 - 6937 (2020/09/15)
An efficient enantioselective synthesis of cyclic α-aminophosphonates via multicomponent reactions of 2-alkynylbenzaldehydes, amines, and dimethylphosphonate has been developed with the use of a chiral silver spirocyclic phosphate as the catalyst. This protocol provides straightforward access to a series of chiral C1-phosphonylated 1,2-dihydroisoquinoline derivatives with high yields (up to 99%) and high enantioselectivities (up to 94% ee) for a broad substrate scope. The products could be further transformed into densely functionalized compounds and corresponding α-aminophosphonic acids.
Catalyst-free ambient temperature synthesis of isoquinoline-fused benzimidazoles from 2-alkynylbenzaldehydes: Via alkyne hydroamination
Mishra, Manisha,Twardy, Dylan,Ellstrom, Clifford,Wheeler, Kraig A.,Dembinski, Roman,T?r?k, Béla
supporting information, p. 99 - 108 (2019/01/11)
An efficient environmentally benign route for the synthesis of benzimidazo[2,1-a]isoquinoline has been developed by reacting 2-ethynylbenzaldehyde and related substituted alkynylbenzaldehydes with variously substituted ortho-phenylenediamines and aliphatic amines in ethanol. This method provides a convenient, room temperature, atom-economical, and catalyst-free access to diversely substituted isoquinoline fused benzimidazoles. Regioselectivity of the reaction, as referred to o-phenylenediamines, was confirmed by X-ray crystallography. The reaction was found to occur in three major steps (imine formations, cyclization, and aromatization) and a mechanism has been proposed.
Visible-Light-Promoted Generation of α-Ketoradicals from Vinyl-bromides and Molecular Oxygen: Synthesis of Indenones and Dihydroindeno[1,2-c]chromenes
Pagire, Santosh K.,Kreitmeier, Peter,Reiser, Oliver
supporting information, p. 10928 - 10932 (2017/08/30)
Ortho-alkynylated α-bromocinnamates can be converted by a visible-light-mediated photocascade reaction with molecular oxygen into either indenones or dihydroindeno[1,2-c]chromenes. The one-step process features key photochemical steps, that is, the initial activation of vinyl bromides through energy transfer to give α-ketoradicals in a reaction with molecular oxygen, followed by α-oxidation of an arene moiety by 6-π electrocyclization, and subsequent hydroxylation by an electron-transfer process from the same photocatalyst leads to the dihydroindeno[1,2-c]chromenes.
Gold-Catalyzed Ring Expansion of Enyne-Lactone: Generation and Transformation of 2-Oxoninonium
Luo, Kui,Cao, Tongxiang,Jiang, Huanfeng,Chen, Lianfen,Zhu, Shifa
supporting information, p. 5856 - 5859 (2017/11/10)
An efficient gold-catalyzed ring-expansion reaction of enyne-lactones to form 2-oxoninonium intermediates is reported. The 2-oxoninonium generated in this work could undergo further 6π electrocyclization and aromatization reaction to produce different aromatic compounds.
