scholarly journals Dipyrazolo[1,5-a:4',3'-c]pyridines – a new heterocyclic system accessed via multicomponent reaction

2012 ◽  
Vol 8 ◽  
pp. 2223-2229 ◽  
Author(s):  
Wolfgang Holzer ◽  
Gytė Vilkauskaitė ◽  
Eglė Arbačiauskienė ◽  
Algirdas Šačkus
Keyword(s):  
Hydrogen Atom ◽  
Multicomponent Reaction ◽  
Heterocyclic System ◽  
Silver Triflate ◽  
Spectroscopic Investigations ◽  
Tricyclic Compounds

The synthesis of dipyrazolo[1,5-a:4',3'-c]pyridines is described. Easily obtainable 5-alkynylpyrazole-4-carbaldehydes, p-toluenesulfonyl hydrazide, and an aldehyde or ketone containing an α-hydrogen atom were reacted in a silver triflate catalyzed multicomponent reaction affording new tricyclic compounds with a dipyrazolo[1,5-a:4',3'-c]pyridine core. Detailed NMR spectroscopic investigations (1H, 13C and 15N) were undertaken with all obtained compounds.

scholarly journals Synthesis of trifluoromethyl-substituted pyrazolo[4,3-c]pyridines – sequential versus multicomponent reaction approach

2014 ◽  
Vol 10 ◽  
pp. 1759-1764 ◽  
Author(s):  
Barbara Palka ◽  
Angela Di Capua ◽  
Maurizio Anzini ◽  
Gyté Vilkauskaité ◽  
Algirdas Šačkus ◽  
...  
Keyword(s):  
Multicomponent Reaction ◽  
Cross Coupling ◽  
Terminal Alkynes ◽  
One Pot ◽  
Silver Triflate ◽  
Microwave Assisted ◽  
Spectroscopic Investigations ◽  
Coupling Conditions ◽  
Substituted 1

A straightforward synthesis of 6-substituted 1-phenyl-3-trifluoromethyl-1H-pyrazolo[4,3-c]pyridines and the corresponding 5-oxides is presented. Hence, microwave-assisted treatment of 5-chloro-1-phenyl-3-trifluoromethylpyrazole-4-carbaldehyde with various terminal alkynes in the presence of tert-butylamine under Sonogashira-type cross-coupling conditions affords the former title compounds in a one-pot multicomponent procedure. Oximes derived from (intermediate) 5-alkynyl-1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carbaldehydes were transformed into the corresponding 1H-pyrazolo[4,3-c]pyridine 5-oxides by silver triflate-catalyzed cyclization. Detailed NMR spectroscopic investigations (1H, 13C, 15N and 19F) were undertaken with all obtained products.

SPECTROSCOPIC INVESTIGATIONS OF FERROCENE AND RELATED DERIVATIVES

1976 ◽  
Vol 37 (C6) ◽  
pp. C6-463-C6-470 ◽  
Author(s):  
A. TRAUTWEIN ◽  
R. RESCHKE ◽  
I. DÉZSI ◽  
F. E. HARRIS
Keyword(s):  
Spectroscopic Investigations

Measurement of the Lamb shift in the hydrogen atom

1982 ◽  
Vol 138 (10) ◽  
pp. 347 ◽  
Author(s):  
Yurii L. Sokolov ◽  
V.P. Yakovlev
Keyword(s):  
Hydrogen Atom ◽  
Lamb Shift

Direct Cyclization of Alkenyl Thioester via Transition Metal‐hydrogen Atom Transfer/radical‐polar Crossover Mechanism

2019 ◽  
Author(s):  
Shiori Date ◽  
Kensei Hamasaki ◽  
Karen Sunagawa ◽  
Hiroki Koyama ◽  
Chikayoshi Sebe ◽  
...  
Keyword(s):  
Natural Products ◽  
Hydrogen Atom ◽  
Transition Metal ◽  
Hydrogen Atom Transfer ◽  
Synthetic Method ◽  
Atom Transfer ◽  
Reaction Conditions ◽  
Hydride Hydrogen ◽  
Sulfur Heterocycles ◽  
One Step

<div>We report here a catalytic, Markovnikov selective, and scalable synthetic method for the synthesis of saturated sulfur heterocycles, which are found in the structures of pharmaceuticals and natural products, in one step from an alkenyl thioester. Unlike a potentially labile alkenyl thiol, an alkenyl thioester is stable and easy to prepare. The powerful Co catalysis via a cobalt hydride hydrogen atom transfer and radical-polar crossover mechanism enabled simultaneous cyclization and deprotection. The substrate scope was expanded by the extensive optimization of the reaction conditions and tuning of the thioester unit.</div>

Synthesis of Spongidine A, D and Petrosaspongiolide L Methyl Ester Using Pyridine C-H Functionalization

2019 ◽  
Author(s):  
Florian Bartels ◽  
Manuela Weber ◽  
Mathias Christmann
Keyword(s):  
Natural Products ◽  
Methyl Ester ◽  
Hydrogen Atom ◽  
Phospholipase A2 ◽  
Late Stage ◽  
Hydrogen Atom Transfer ◽  
Ring System ◽  
Tetracyclic Core ◽  
Intramolecular Hydrogen ◽  
Phospholipase A2 Inhibitors

<div>An efficient strategy for the synthesis of the potent phospholipase A2 inhibitors spongidine A and D is presented. The tetracyclic core of the natural products was assembled via an intramolecular hydrogen atom transfer‐initiated Minisci reaction. A divergent late‐stage functionalization of the tetracyclic ring system was also used to achieve a concise synthesis of petrosaspongiolide L methyl ester.</div>

Catalytic Synthesis of Cyclic Guanidines via Hydrogen Atom Transfer and Radical-Polar Crossover

2020 ◽  
Author(s):  
Shunya Ohuchi ◽  
Hiroki Koyama ◽  
Hiroki Shigehisa
Keyword(s):  
Hydrogen Atom ◽  
Functional Group ◽  
Hydrogen Atom Transfer ◽  
Catalytic Synthesis ◽  
Membered Ring ◽  
Biologically Active ◽  
Atom Transfer ◽  
Powerful Method ◽  
Protective Groups ◽  
The Common

A catalytic synthesis of cyclic guanidines, which are found in many biologically active compounds and natu-ral products, was developed, wherein transition-metal hydrogen atom transfer and radical-polar crossover were employed. This mild and functional-group tolerant process enabled the cyclization of alkenyl guanidines bearing common protective groups, such as Cbz and Boc. This powerful method not only provided the common 5- and 6-membered rings but also an unusual 7-membered ring. The derivatization of the products afforded various heterocycles. We also investigated the se-lective cyclization of mono-protected or hetero-protected (TFA and Boc) alkenyl guanidines and their further derivatiza-tions.

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