Search results for "DERIVATIVES"

Heterocyclic rearrangements. Phenylhydrazones andN-methyl-N-phenylhydrazones of 3-acylisoxazoles

1983

The reaction of 3-benzoyl-5-phenylisoxazole (4) and 3-acetyl-5-methylisoxazole (5) with phenylhydrazine and N-methyl-N-phenylhydrazine has been investigated and the reactivity of (E)- and (Z)-phenylhydrazones and N-methyl-N-phenylhydrazones has been studied.

ChemInform Abstract: The Pyrrole Moiety as a Template for COX-1/COX-2 Inhibitors.

2000

ChemInform Abstract: Ru(bpy)2Cl2: A Catalyst Able to Shift the Course of the Photorearrangement in the Boulton-Katritzky Reaction.

2016

Abstract The Boulton–Katritzky reaction represents one of the most popular and efficient strategies used to realize azole-into-azole conversions. For example, under different experimental conditions, it allows the rearrangement of Z-arylhydrazones of 3-benzoyl-5-phenyl-1,2,4-oxadiazoles (1) into 2-aryl-4-benzoylamino-5-phenyl-2H-1,2,3-triazoles (2) in very high yields. Moreover, we have recently realized this conversion also by UV-photostimulation. Now we have enlarged the scope of the reaction irradiating with visible or UV light an acetonitrile solution of some Z-arylhydrazones (1a–e) in the presence of catalytic amounts of Ru(bpy)2Cl2. We have observed the unexpected formation of the 1-a…

ChemInform Abstract: Cyclocondensation of α-Aminonitriles and Enones: A Short Access to 3,4-Dihydro-2H-pyrrole 2-Carbonitriles and 2,3,5-Trisubstitut…

2010

The reaction of α,β-unsaturated carbonyl compounds with aminoacetonitrile hydrochloride furnishes 3,5-disubstituted 3,4-dihydro-2H-pyrrole-2-carbonitriles in a one-pot reaction sequence. While these products can serve as starting materials for the preparation of polysubstituted pyrrolizidines, they are kinetically stable against the base-induced elimination of HCN. In contrast, their 2-substituted analogues obtained from α-substituted α-aminonitriles can be readily converted to the corresponding 2,3,5-trisubstituted pyrroles under microwave irradiation. The key step presumably involves the thermal electrocyclization of a stabilized 2-azapentadienyl anion formed by condensation of the reacta…

Addition of α-Aminonitriles to α,β-Unsaturated Carbonyl Compounds: A One-Pot Synthesis of Polysubstituted Pyrrolidines.

2003

The vinylogous addition of deprotonated N-alkyl-α-aminonitriles to α,β-unsaturated carbonyl compounds yields cyclic intermediates which can be reduced to form polysubstituted pyrrolidines in a one-pot reaction sequence. Since the cyano substituent is lost in the reduction step, the aminonitriles serve as easily accessible (N-alkylamino)-substituted carbanion equivalents.

Dielektrische Relaxation und aromatischer Bindungszustand der Amino- und Hydroxylgruppe

1965

Bei funf Wellenlangen im Bereich von 60 cm bis 7 mm wurde in benzolischer Losung bei 20 °C die dielecktrische Absorption von Benzolderivaten gemessen, die Amino- oder Hydroxylgruppen enthalten. Danach erfolgt die elektrische Dipolorientierung bei N, N'-Dimethylanilin, Diphenylamin und ver wandten Molekulen in der Art, das die drei Bindungen des Stickstoffs uber die ebene Anordnung hinweg umklappen. Ebenso kann auch das Relaxationsverhalten von Anilin beschrieben werden. Voraussetzung fur diese Inversion ist die mesomere Wechselwirkung zwischen dem Stickstoff und einem aromatischen ϕ-Elektronen-system. Dagegen ergeben die Meswerte keinen Hinweis darauf, das bei der Hydroxylgruppe auch eine s…

Multi-Arm 1,2,3-Thiadiazole Systems

1997

Benzene derivatives 2a–c with 6, 4, and 3 side chains bearing terminal 1,2,3-thiadiazole rings, respectively, have been prepared. Alkaline cleavage of 2a–c led to the corresponding alkynethiolates 6a–c, which were trapped by electrophiles such as benzyl bromide or iodomethane. The method provides an alternative to the thermal or photochemical cleavage of 1,2,3-thiadiazoles to thioketenes, which react further with nucleophiles.

Reactions of 4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidines with α,β-unsaturated carbonyl compounds

2004

The reaction of 5,7-diphenyl-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine (1) with α,β-unsaturated carbonyl compounds 2a-f led to the formation of the alkylated heterocycles 3a-f (Figure 1). However, the reaction of 5-methyl-7-phenyl-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine (5) with 2a-c yielded under the same conditions the triazolo[5,1-b]quinazolines 6a-c (Figure 3). In this case, the alkylation is followed by a cyclocondensation. The structure elucidation of the products is based on ir, ms, 1H and 13C nmr measurements and on an X-ray diffraction study.

ChemInform Abstract: A New Tandem Cross Metathesis-Intramolecular Aza-Michael Reaction for the Synthesis of α,α-Difluorinated Lactams.

2012

Difluorinated amides are treated with methyl vinyl ketone or analogous esters to produce the desired γ- and δ-lactam units including optically active versions.

ChemInform Abstract: Approaches for the Introduction of Fluorinated Substituents into [1,2,3]Triazolo[1,5-a]pyridines.

2014

Functionalization of [1,2,3]triazolo[1,5-a]pyridines with a trifluoromethyl group is achieved for the first time.