Synthesis of 2,3-dihydropyrroles by photo rearrangement of Hantzsch 1,4-dihydropyridines with high diastereoselectivity

Zhong, Qi‐Di; Fan, Qiangwen; Yan, Hong

doi:10.1016/j.tetlet.2017.02.041

Cited by 17 publications

(8 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To date, photochemical reactions have been applied to various fields of organic chemistry as ecofriendly and efficient synthesis method, including metal catalysis (Condie et al, 2010), green organic synthesis (Yu et al, 2018), total synthesis (Reddy and Rawal, 2000) and asymmetric synthesis (Richard et al, 2015) of compounds. Photosensitive 1,4-dihydropyridine is often used as a photoreactive substrate for various reactions under light-induced conditions, such as photoinduced rearrangement (Zhong et al, 2017), aromatization (Memarian and Mirjafari, 2005), and [2+2] photocycloaddition reactions (Eisner et al, 1970;Hilgeroth et al, 2000;Hilgeroth and Baumeister, 2001). Unexpectedly, the photoreaction product of 1,4dihydropyridine we obtained was distinct from that reported previously.…”

Section: Introductioncontrasting

confidence: 60%

Visible-Light-Induced C–C Coupling Reaction to Synthesize Bipyridine From 3-Cyano-1,4-Dihydropyridines

et al. 2020

Self Cite

View full text Add to dashboard Cite

A concise and efficient photocatalytic CC coupling of 1-benzyl-3-cyano-1, 4-dihydropyridine for synthesis of 1,1 ′-dibenzyl-3, 3 ′-dicyano-1,1 ′ ,4,4 ′-tetrahydro-4, 4 ′-bipyridine is described. The reporter system provides a novel technique that facilitates synthesis of CC coupling derivatives without addition of transition metals and oxidants or other additives. A plausible synthetic pathway is proposed, and the coupling product was characterized via nuclear magnetic resonance spectroscopy (1 H and 13 C NMR), high-resolution electrospray ionization mass spectrometry (ESI-HRMS) and X-ray analyses.

show abstract

Section: Introductioncontrasting

confidence: 60%

Visible-Light-Induced C–C Coupling Reaction to Synthesize Bipyridine From 3-Cyano-1,4-Dihydropyridines

et al. 2020

Self Cite

View full text Add to dashboard Cite

show abstract

“…Colorless crystal, yield: 23% (0.38 g); 1 H NMR (400 MHz, DMSO-d 6 ) δ (ppm): 5.26−5.41 (m, 4H), 4.87−4.96 (m, 4H),1.94−2.06 (m, 12H). 13 1,1′,1″,1‴- (3,6,9,4.0.0 2,7 .0 4,11 .0 5,10 ]dodecane-3,6,9,12-tetrayl)tetrakis(propan-1-one) (3b). Colorless crystal, yield: 25% (0.49 g); 1 H NMR (400 MHz, DMSO-d 6 ) δ (ppm): 5.31−5.43 (m, 4H), 4.94−5.02 (m, 4H), 2.23−2.37 (m, 8H), 0.88−0.97 (m, 12H).…”

Section: ■ Conclusionmentioning

confidence: 99%

Visible-Light-Driven [2 + 2] Photocycloaddition for Constructing Dimers of N,N′-Diacyl-1,4-dihydropyrazines: Experimental and Theoretical Investigation

Zhang,

Wei,

Chu

et al. 2023

J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

In this study, the visible-light-driven [2 + 2] photocycloaddition of 1,4-dihydropyrazines in solution was reported. The N,N′-diacyl-1,4-dihydropyrazines with different substituents showed completely different reactivity under the irradiation of a 430 nm blue light-emitting diode (LED) lamp. N,N′-Diacetyl-1,4-dihydropyrazine and N,N′-dipropionyl-1,4-dihydropyrazine were the only compounds capable of undergoing a [2 + 2] photocycloaddition reaction, yielding syn-dimers and cage-dimers (known as 3,6,9,12-tetraazatetraasteranes) with overall yields of 76 and 83%, correspondingly. The substituent-reactivity effect on [2 + 2] photocycloaddition of N,N′-diacyl-1,4-dihydropyrazines was investigated by density functional theory calculations. The results show that the substituents have little influence on Gibbs free energy for the [2 + 2] photocycloaddition and mainly affect the excited energy, reaction sites, and the triplet excited-state structures of 1,4-dihydropyrazines, which are closely related to whether the reaction occurs. The results offer insights into the photochemical reactivity of 1,4-dihydropyrazines and an approach for constructing dimers of N,N′-diacyl-1,4-dihydropyrazines through a solution-based visible-light-driven [2 + 2] photocycloaddition, especially for the construction of 3,6,9,12-tetraazatetraasteranes. Compared with the solid-state [2 + 2] photocycloaddition of 1,4-dihydropyrazine, this photocycloaddition will be an efficient and environmentally friendly method for synthesizing tetraazatetraasteranes with the advantages of milder reaction conditions, simple operation, adjustable reaction amounts by omitting the cocrystal growth step, etc.

show abstract

“…Subsequently, a variety of acids, including AcOH, TsOH, TfOH, and HI (45% aq), as well as Lewis acidic FeCl 3 and AlCl 3 , were investigated in the reaction, but all resulted in lower yields of benzo[f]isoindole-4,9-dione 4a (Table 1, entries 8-13). Next, examination of different solvents revealed that toluene showed the best performance, and that other solvents tested were inferior to toluene with regard to the yield of the desired product 4a (dimethylformamide (DMF; 50%), dimethyl sulfoxide (DMSO; 52%), tetrahydrofuran (THF; 55%), MeCN (51%), and dichloromethane (DCM; 33%)) (Table 1, entries [14][15][16][17][18]. Furthermore, when we reduced the number of equivalents of benzaldehyde (2a) and diethyl iminodiacetate (3a), the yield of the product 4a decreased (Table 1, entries 19 and 20).…”

Section: Acid-induced Intermolecular [3+2]mentioning

confidence: 99%

“…Due to their wide utility as biologically active agents and key intermediates in organic synthesis, pyrrole derivatives have attracted significant attention from organic chemists, and a variety of efficient methods have been developed for their synthesis. Examples include Hantzsch, [13][14][15][16][17][18] Trofimov, [19][20][21][22] Mannich [23][24][25][26] and Clauson-Kaas reactions, [27][28][29][30] Friedel-Crafts, [31][32][33][34] and [3+2] cycloadditions. [35][36][37][38][39] In recent years, metal-free catalysis of various organic transformations has gained more and more attention.…”

Section: Introductionmentioning

confidence: 99%

Acid-induced intermolecular [3+2] cycloaddition/oxidation to synthesize polysubstituted benzo[f]isoindole-4,9-diones

Lin

et al. 2019

Journal of Chemical Research

View full text Add to dashboard Cite

A novel one-pot 1,3-dipolar cycloaddition/oxidation reaction of 1,4-quinones, aromatic aldehydes, and N-substituted amino esters to construct polysubstituted benzo[ f]isoindole-4,9-diones induced by benzoic acid is reported. Based on optimized reaction conditions, various polysubstituted benzo[ f]isoindole-4,9-diones derivatives are obtained in moderate yields. This straightforward methodology employs mild reaction conditions, a green oxidant, and readily available starting materials. Notably, a wide range of substrates is tolerated.

show abstract

Synthesis of 2,3-dihydropyrroles by photo rearrangement of Hantzsch 1,4-dihydropyridines with high diastereoselectivity

Cited by 17 publications

References 42 publications

Visible-Light-Induced C–C Coupling Reaction to Synthesize Bipyridine From 3-Cyano-1,4-Dihydropyridines

Visible-Light-Induced C–C Coupling Reaction to Synthesize Bipyridine From 3-Cyano-1,4-Dihydropyridines

Visible-Light-Driven [2 + 2] Photocycloaddition for Constructing Dimers of N,N′-Diacyl-1,4-dihydropyrazines: Experimental and Theoretical Investigation

Acid-induced intermolecular [3+2] cycloaddition/oxidation to synthesize polysubstituted benzo[f]isoindole-4,9-diones

Contact Info

Product

Resources

About