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o-Nitrobenzyl Oxime Ethers Enable Photoinduced Cyclization Reaction to Provide Phenanthridines under Aqueous Conditions.

Organic Letters, 2023
In this paper, we describe a novel N-O photolysis of o-nitrobenzyl oxime ethers that enables the synthesis of phenanthridines via intramolecular cyclization reactions. Without the use of additional photocatalysts or photosensitizers, the process proceeds
Hidenori Okamura   +3 more
semanticscholar   +1 more source

Regioselective Synthesis of Phenanthridines via Pd(II)-Catalyzed Annulative C(sp2)-H Activation.

Journal of Organic Chemistry, 2023
A robust synthesis of phenanthridines has been described via Pd(II)-catalyzed domino C(sp2)-H activation/N-arylation using oxime esters with aryl acyl peroxides in a highly regioselective manner.
Anamika Yadav   +3 more
semanticscholar   +1 more source

NHC-Catalyzed Tandem Reaction: A Strategy for the Synthesis of 2-Pyrrolidinone-Functionalized Phenanthridines.

Journal of Organic Chemistry, 2023
Herein, an N-heterocyclic carbene (NHC)-catalyzed tandem cyclization/addition/cyclization reaction of 2-isocyanobiaryls and α-bromo-N-cinnamylamides for the synthesis of 2-pyrrolidinone-functionalized phenanthridines is developed.
N. Zhou   +5 more
semanticscholar   +1 more source

Photochemical Synthesis of Succinic Ester-Containing Phenanthridines from Diazo Compounds as 1,4-Dicarbonyl Precursors.

Organic Letters, 2022
We disclosed herein a straightforward photochemical method for the construction of phenanthridines containing a synthetically useful succinate unit. The reaction occurred under visible-light irradiation with cheap eosin Y Na as photoredox catalyst and a ...
Haiwei Ye   +4 more
semanticscholar   +1 more source

Metal-Free Generation of γ-Cyanoalkyl Radicals by N-Heterocyclic Carbene Catalysis: Assembly of 6-Cyanoalkyl Phenanthridines.

Organic Letters, 2022
A number of γ-cyanoalkyl radicals were generated by sustainable N-heterocyclic carbene catalysis in tin-, transition-meal-, and light-free conditions, followed by insertion into biaryl isonitriles, thus leading to the rapid assembly of a variety of ...
Qianrong Li   +2 more
semanticscholar   +1 more source

Redox-Neutral Generation of Iminyl Radicals by N-Heterocyclic Carbene Catalysis: Rapid Access to Phenanthridines from Vinyl Azides.

Organic Letters, 2022
An N-heterocyclic carbene-catalyzed oxidant-, metal- and light-free iminyl radical generation pathway stemming from the reaction of vinyl azide and α-bromo ester is uncovered.
Lixia Liu, Qijing Zhang, Chengming Wang
semanticscholar   +1 more source

Redetermination of the structure of phenanthridine [PDF]

open access: possibleActa Crystallographica Section C Crystal Structure Communications, 1993
C 13 H 9 N, M r =179.22, orthorhombic, P2 1 2 1 2 1 , a=4.872 (2), b=11.526 (4), c= 15.811 (4) A, V=887.7 (5) A 3 , Z=4, D x = 1.341 Mg m -3 , λ(Mo Kα)=0.71069 A, μ= 0.07 mm -1 , F(000)=376, T=110 K, final R=0.045 for 1713 observed reflections. Phenanthridine was found to be planar in the solid state with a mean deviation of 0.002 A from the mean plane
Brett, W.a.   +2 more
openaire   +1 more source

Visible Light-Promoted Radical-Mediated Ring-Opening/Cyclization of Vinyl Benzotriazoles: An Alternative Approach to Phenanthridines.

Organic Letters, 2022
A visible light-promoted radical-mediated ring-opening/cyclization of vinyl benzotriazoles has been developed. The method provides an efficient and practical approach to synthesize functionalized phenanthridines from vinyl benzotriazoles with alkyl ...
Jiaqi Li   +3 more
semanticscholar   +1 more source

Synthesis of C8-Aminated Pyrrolo-Phenanthridines or -Indoles via Series C(sp2 or sp3)-H Activation and Fluorescence Study.

Organic Letters, 2022
This report developed a method for the synthesis of C8-aminated pyrrolo-phenanthridines or -indoles by series ortho C(sp2)-H amination/ipso C(sp2)-H or C(sp3)-H arylation.
Bo-Sheng Zhang   +7 more
semanticscholar   +1 more source

Bischler-Napieralski Synthesis of 6-Alkynyl Phenanthridines Based on Tf2O-Promoted Electrophilic Activation of N-Aryl-2-propynamides.

Journal of Organic Chemistry, 2021
An efficient method for the synthesis of 6-alkynyl phenanthridines was developed. The method offered the first example to use 2-propynamides as substrates in the Bischler-Napieralski reaction and to create alkynylnitrilium triflates as new active ...
L. Shan   +5 more
semanticscholar   +1 more source

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