23589-63-1Relevant academic research and scientific papers
A CONVENIENT PRECURSOR TO 3,4-DIDEHYDROPYRIDINE
May, Christopher,Moody, Christopher J.
, p. 2123 - 2124 (1985)
The preparation of 3-(3,3-dimethyltriazen-1-yl)pyridine-4-carboxylic acid (5), a convenient shelf-stable precursor to 3,4-didehydropyridine, is described.
Rhodaelectrocatalysis for Annulative C?H Activation: Polycyclic Aromatic Hydrocarbons through Versatile Double Electrocatalysis
Kong, Wei-Jun,Finger, Lars H.,Oliveira, Jo?o C. A.,Ackermann, Lutz
supporting information, p. 6342 - 6346 (2019/04/08)
Rapid access to structurally diversified polycyclic aromatic hydrocarbons (PAHs) in a controlled manner is of key significance in materials sciences. Herein, we describe a strategy featuring two distinct electrocatalytic C?H transformations for the synthesis of novel nonplanar PAHs. The combination of rhodaelectrooxidative C?H activation/[2+2+2] alkyne annulation of easily accessible boronic acids with electrocatalytic cyclodehydrogenation provided modular access to diversely substituted PAHs with electricity as a sustainable oxidant. The unique molecular topology as well as the photophysical and electronic properties of the thus obtained PAHs were fully analyzed. The unique power of this metallaelectrocatalysis method was demonstrated by the chemoselective assembly of synthetically useful iodo-substituted PAHs.
Solvent free, phosphine free Pd-catalyzed annulations of aryl bromides with diarylacetylenes
Bej, Ansuman,Chakraborty, Amarnath,Sarkar, Amitabha
, p. 15812 - 15819 (2013/09/12)
Palladium nanoparticles and sodium acetate catalyze the reaction of aryl bromide with diarylacetylene to produce annulated products in good yield. One equivalent of PEG-600 serves as the solvent. This procedure is compatible with a wide variety of functional groups.
Synthesis of highly substituted acenes through rhodium-catalyzed oxidative coupling of arylboron reagents with alkynes
Fukutani, Tatsuya,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
scheme or table, p. 2867 - 2874 (2011/05/28)
The rhodium-catalyzed oxidative 1:2 coupling reactions of arylboronic acids or their esters with alkynes smoothly proceed to produce the corresponding annulated products. Of special note, highly substituted, readily soluble, and tractable anthracene and tetracene derivatives can be obtained selectively from 2-naphthyl- and 2-anthrylboron reagents, respectively.
SYNTHETIC CONNECTIONS TO THE DIRECTED ortho METALATION REACTION. 3,4-PYRIDINES FROM 4-TRIALKYLSILYL-3-PYRIDYL TRIFLATES
Tsukazaki, Masao,Snieckus, Victor
, p. 533 - 536 (2007/10/02)
4-Trialkylsilyl-3-pyridyl triflates (11a-b), derived from 9 and 12 by directed ortho metalation chemistry, serve as useful precursors of 3,4-pyridines (6a-b) and lead by cycloaddition and nucleophilic trapping reactions to products (13a-b, 14a-b, 15, 16a-b, and 17a-b).
A NEW PRECURSOR TO 3,4-DIDEHYDROPYRIDINE, AND ITS USE IN THE SYNTHESIS OF THE ANTITUMOR ALKALOID ELLIPTICINE
May, Christopher,Moody, Christopher J.
, p. 247 - 250 (2007/10/02)
A concise synthesis of the antitumor alkaloid ellipticine (1) is reported.The route involves a Diels-Alder reaction between 1,4-dimethylpyranoindol-3-one (3), easily prepared in two steps from indole, and 3,4-didehydropyridine (4), and for its successful execution required the development of a new thermal, reagent-free precursor to the aryne.This precursor, 3-(3,3-dimethyltriazen-1-yl)pyridine-4-carboxylic acid (10a), prepared from 3-aminopyridine-4-carboxylic acid, decomposes in boiling acetonitrile to generate 3,4-didehydropyridine which can be intercepted in Diels-Alder reactions with tetraphenylcyclopentadienone, furan, and 2,5-dimethylfuran.The triazenes (10b) and (10c) can be prepared and decomposed similarly.The key Diels-Alder reaction between the pyranoindolone (3) and 3,4-didehydropyridine (4) gives ellipticine (1) in 20 percent yield, together with an equal amount of isoellipticine (14).
