1,4-Dihydro-1-Methyl-7-(2-(5-Nitro-2-Furyl)Vinyl)-4-Oxo-1,8-Naphthyridine-3-Carboxylic Acid, Potassium Salt 29676-95-7

2012 ◽  
Keyword(s):  
Carboxylic Acid ◽  
Potassium Salt

Epoxides as Dual-Functionalized Alkylating Reagents in Catellani Reactions for the Assembly of Heterocycles

Synlett ◽  
2020 ◽  
Vol 31 (09) ◽  
pp. 829-837 ◽  
Author(s):  
Hong-Gang Cheng ◽  
Qianghui Zhou ◽  
Chenggui Wu
Keyword(s):  
Carboxylic Acid ◽  
Catalytic System ◽  
Potassium Salt ◽  
Salient Features ◽  
Alkylating Reagents ◽  
Straightforward Approach

Reported is a cooperative catalytic system consisting of a complex of Pd with dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (XPhos) and the potassium salt of 5-norbornene-2-carboxylic acid that permits the use of epoxides as dual-functionalized alkylating reagents in Catellani-type reactions for the assembly of heterocycles. Salient features of this research include readily available substrates, use of the potassium salt of 5-norbornene-2-carboxylic acid as a catalytic mediator as well as a base, and excellent regioselectivity for the cleavage of epoxides. This mild, chemoselective, scalable, atom- and step-economic protocol offers a straightforward approach for the assembly of isochroman and 2,3-dihydrobenzofuran scaffolds.

Structural Studies on Bioactive Compounds. Part 38.1 Reactions of 5-Aminoimidazole-4-Carboxamide: Synthesis of Imidazo[1,5-a]Quinazoline-3-Carboxamides

2003 ◽  
Vol 2003 (7) ◽  
pp. 398-401 ◽  
Author(s):  
Duncan R. Hannah ◽  
Malcolm F. G. Stevens
Keyword(s):  
Carboxylic Acid ◽  
Schiff Bases ◽  
Bioactive Compounds ◽  
Potassium Salt ◽  
Sodium Hydride ◽  
Aromatic Aldehydes ◽  
Deuterium Exchange ◽  
Structural Studies

5-Aminoimidazole-4-carboxamide reacts with aromatic aldehydes to afford Schiff bases which can be cyclised to imidazo[1,5- a]quinazoline-3-carboxamides in DMF/sodium hydride. The potassium salt of imidazo[1,5- a]quinazoline-3-carboxylic acid undergoes deuterium exchange in D2O at the 1-position.

scholarly journals Carbenoid-mediated nucleophilic “hydrolysis” of 2-(dichloromethylidene)-1,1,3,3-tetramethylindane with DMSO participation, affording access to one-sidedly overcrowded ketone and bromoalkene descendants§

2014 ◽  
Vol 10 ◽  
pp. 307-315 ◽  
Author(s):  
Rudolf Knorr ◽  
Thomas Menke ◽  
Johannes Freudenreich ◽  
Claudio Pires
Keyword(s):  
Carboxylic Acid ◽  
Dicarboxylic Acid ◽  
Oxygen Transfer ◽  
Potassium Salt ◽  
Dimethyl Sulfide ◽  
Lithium Salt ◽  
Rotational Mobility ◽  
Tertiary Alcohols ◽  
Information File ◽  
Hydrolysis Of

2-(Dichloromethylidene)-1,1,3,3-tetramethylindane was “hydrolyzed” by solid KOH in DMSO as the solvent at ≥100 °C through an initial chlorine particle transfer to give a Cl,K-carbenoid. This short-lived intermediate disclosed its occurrence through a reversible proton transfer which competed with an oxygen transfer from DMSO that created dimethyl sulfide. The presumably resultant transitory ketene incorporated KOH to afford the potassium salt of 1,1,3,3-tetramethylindan-2-carboxylic acid (the product of a formal hydrolysis). The lithium salt of this key acid is able to acylate aryllithium compounds, furnishing one-sidedly overcrowded ketones along with the corresponding tertiary alcohols. The latter side-products (ca. 10%) were formed against a substantially increasing repulsive resistance, as testified through the diminished rotational mobility of their aryl groups. As a less troublesome further side-product, the dianion of the above key acid was recognized through carboxylation which afforded 1,1,3,3-tetramethylindan-2,2-dicarboxylic acid. Brominative deoxygenation of the ketones furnished two one-sidedly overcrowded bromoalkenes. Some presently relevant properties of the above Cl,K-carbenoid are provided in Supporting Information File 1.

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