Recent Progress in the Synthesis and Applications of Heterocycles Derived from Enaminonitriles

Bondock, Samir; Tarhoni, Abd El‐Gaber; Fadda, Ahmed A.

doi:10.2174/138527211794519041

Cited by 23 publications

(3 citation statements)

References 123 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[12,13] Enaminonitriles [14,15] are valuable building blocks in synthetic organic chemistry that have been employed to access different nitrile-containing compounds. In fact, the number of nitrile-containing drug leads is vast.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of 5‐oxo‐5H‐chromeno[3,4‐c]pyridine‐1‐carbonitriles and features of their NMR spectra

Shkoor

Ahmed

et al. 2019

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

Two different methods leading to 5-oxo-5H-chromeno[3,4-c]pyridine-1carbonitriles were investigated. Reactions of 3-aminocrotonirile with substituted salicylaldehydes provided 5-oxo-5H-chromeno[3,4-c]pyridine-1carbonitriles with the same substituent on positions 2 and 4 of the system. The reaction of 3-aminocrotonirile with variety of substituted 3acetylcoumarins lead to 5-oxo-5H-chromeno[3,4-c]pyridine-1-carbonitriles with different substituents on positions 2 and 4. The structures of the products were confirmed by spectroscopic methods. The presence of nitrile moiety in the structures with fixed geometry caused the highly downfield shift of the aromatic proton at position 10 in 1 H NMR spectrum. The electronic factor of the substituents caused variation of this downfield shift.

show abstract

Section: Introductionmentioning

confidence: 99%

“…Nitrile group possesses unique structural features and properties that render it as an important pharmacophore. [12,13] Enaminonitriles [14,15] are valuable building blocks in synthetic organic chemistry that have been employed to access different nitrile-containing compounds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 5‐oxo‐5H‐chromeno[3,4‐c]pyridine‐1‐carbonitriles and features of their NMR spectra

Shkoor

Ahmed

et al. 2019

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

“…Moreover, amines and activated acetonitriles can serve as starting materials for the synthesis of β‐enaminonitriles in the presence of triethyl orthoformate [Scheme , Eq. (2)] 1b. However, the above‐mentioned methods usually require harsh conditions.…”

Section: Introductionmentioning

confidence: 99%

Light Energy Collection in a Porphyrin–Imide–Corrole Ensemble

Ciuciu¹,

Flamigni²,

Voloshchuk³

et al. 2013

Chemistry An Asian Journal

View full text Add to dashboard Cite

An assembly consisting of three units, that is, a meso-substituted corrole (C3), 1,8 naphthaleneimide (NIE), and a Zn porphyrin (ZnP), has been synthesized. NIE is connected to C3 through a 1,3-phenylene bridge and to the ZnP unit through a direct C-C bond. The convergent synthetic strategy includes the preparation of a trans-A2B-corrole possessing the imide unit, followed by Sonogashira coupling with a meso-substituted A3B-porphyrin. The photophysical processes in the resulting triad ZnP-NIE-C3 are examined and compared with those of the corresponding C3-NIE dyad and the constituent reference models C3, NIE, and ZnP. Excitation of the NIE unit in C3-NIE leads to a fast energy transfer of 98 % efficiency to C3 with a rate k(en) =7.5×10(10) s(-1), whereas excitation of the corrole unit leads to a reactivity of the excited state identical to that of the model C3, with a deactivation rate to the ground state k=2.5×10(8) s(-1). Energy transfer to C3 and to ZnP moieties follows excitation of NIE in the triad ZnP-NIE-C3. The rates are k(en) =7.5×10(10) s(-1) and k(en) =2.5×10(10) s(-1) for the sensitization of the C3 and ZnP unit, respectively. The light energy transferred from NIE to Zn porphyrin unit is ultimately funneled to the corrole component, which is the final recipient of the excitation energy absorbed by the different components of the array. The latter process occurs with a rate k(en) =3.4×10(9) s(-1) and 89 % efficiency. Energy transfer processes take place in all cases by a Förster (dipole-dipole) mechanism. The theory predicts quite satisfactorily the rate for the ZnP/C3 couple, where components are separated by about 23 Å, but results in calculated rates that are one to two orders of magnitude higher for the couples NIE/ZnP (D/A) and NIE/C3, which are separated by distances of about 14 and 10 Å, respectively.

show abstract

Copper‐Catalyzed N‐Aryl‐β‐enaminonitrile Synthesis Utilizing Isocyanides as the Nitrogen Source

Kim

Hong

2015

Adv Synth Catal

View full text Add to dashboard Cite

An ovel synthetic protocol for N-aryl-b-enaminonitriles,w hich are useful building blocks for heterocycle synthesis, was developed using isocyanides as the nitrogen source.U sing copper-catalyzed one-stepr eactions between isocyanides and benzyl cyanidesu nder mild conditions,d iverse N-aryl-b-enaminonitriles could be synthesizedi ne xcellent yields and with high atom-efficiency. N-Alkyl-b-enaminonitriles were also synthesizedi ng ood yields. Am echanism involving an imidoyl-copper intermediate was proposedb ased on mechanistic studies and previous reports. In addition,w ed emonstrated that as ynthesized N-aryl-b-enaminonitrile could be utilized for the synthesiso fab -keto nitrile compound and3 -aminopyrazole.

show abstract

Recent Progress in the Synthesis and Applications of Heterocycles Derived from Enaminonitriles

Cited by 23 publications

References 123 publications

Synthesis of 5‐oxo‐5H‐chromeno[3,4‐c]pyridine‐1‐carbonitriles and features of their NMR spectra

Synthesis of 5‐oxo‐5H‐chromeno[3,4‐c]pyridine‐1‐carbonitriles and features of their NMR spectra

Light Energy Collection in a Porphyrin–Imide–Corrole Ensemble

Copper‐Catalyzed N‐Aryl‐β‐enaminonitrile Synthesis Utilizing Isocyanides as the Nitrogen Source

Contact Info

Product

Resources

About