3-(Hetarylamino)- and 3-[(hetarylmethyl)amino]-isoquinolin-1(2H)-ones

Потиха, Л. М.; Gutsul, R. M.; Ковтуненко, В. А.; Толмачев, А. А.

doi:10.1007/s10593-010-0531-0

Cited by 8 publications

(4 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The purity of the products was monitored by HPLC/MS on an Agilent 1100 instrument with an Agilent LC/MSD SL selective detector (the sample was introduced in a TFA matrix) using electron impact. The physicochemical characteristics and the elemental analysis data of the products are given in Tables 1-3. 3-(4-Methoxyanilino)isoquinolin-1(2H)-one (1a) was obtained according to Ali et al [8], while 3-(4-nitroanilino)isoquinolin-1(2H)-one (1b) was obtained according to our previous procedure [13] and 3-HetNHisoquinolin-1(2H)-ones 2a-f were obtained according to our recent procedure [12].…”

Section: Methodsmentioning

confidence: 99%

“…A distinguishing feature of the 1 H NMR spectrum of salt 13, in addition to the lack of a signal for H-12 proton, is the position of the signal for H-1 proton, which is located in the region shielded by the benzene ring of the 12-Ar substituent and observed upfield (at 6.85 ppm) relative to the corresponding proton, H-5, in starting isocarbostyryl 2c (at 7.49 ppm) [12]. The difference in the chemical shifts of these protons ( ~ 0.64) is comparable to the difference noted for compound 7 ( ~ 0.73,  H-5 in starting 1a is 7.27 ppm [9]) and higher than the difference noted for compounds 4a and 4b ( ~ 0.12 for 4a and  ~ 0.42 for 4b,  H-5 in starting compound 1b is 7.58 ppm [13]).…”

mentioning

confidence: 99%

See 1 more Smart Citation

Condensed isoquinolines. 37.* Heterocyclization using 3-(arylamino)- and 3-(hetarylamino)isoquinolin-1(2H)-ones

Потиха

Gutsul²,

Plaskon

et al. 2011

Chem Heterocycl Comp

Self Cite

View full text Add to dashboard Cite

Cyclization starting from enamines is one of the approaches to the synthesis of nitrogen heterocycles [2]. The enamine properties of some derivatives of 3-aminoisoquinolin-1(2H)-one (3-aminoisocarbostyryl) have also been used for heterocyclization [3]. The fusion of a pyrrole or pyridine ring to face c in these cases has been carried out predominantly by intramolecular acylation or alkylation. In some studies of the properties of 3-amino-2-methyl-and 3-aminoisoquinolin-1(2H)-ones, Ohta [4, 5] and Deady [6] have described the formation of condensed isoquinolines in reactions with aldehydes or ketones. In the present work, we studied the reaction of 3-(arylamino)-and 3-(hetarylamino)isoquinolin-1(2H)-ones with aromatic aldehydes.

show abstract

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

Condensed isoquinolines. 37.* Heterocyclization using 3-(arylamino)- and 3-(hetarylamino)isoquinolin-1(2H)-ones

Потиха

Gutsul²,

Plaskon

et al. 2011

Chem Heterocycl Comp

Self Cite

View full text Add to dashboard Cite

show abstract

“…16 c Of note is that using MPEG-550/H 2 O as the aqueous reaction medium, thioester 3 was converted to bioactive 3-aminoisoquinolinone 33 (Scheme 4b), which was synthesized using extremely toxic sodium cyanide previously. 17 Interestingly, switching to an aqueous surfactant solution led to isoquinoline-1,3-dione 34 in the presence of triethyl amine and pyridine (Scheme 4c).…”

mentioning

confidence: 99%

Photoredox-catalyzed coupling of acyl oxime acetates with thiophenols to give arylthioesters in water at room temperature

Zhu

Zhao

et al. 2022

Green Chem.

View full text Add to dashboard Cite

show abstract

“…the starting 3-aminoisocarbostyryls in different chemical shift ranges and differ in their multiplicity (for 1d,e) [1, 2,9]: 10.5-10.7 (s, H-2), 5.4-5.9 (s, H-4), 7.6-7.9 (s, 3-NH, 1a-c) and 5.4-5.9 ppm (t, 3-NH, 1d,e). The signal for 3-NH proton is lacking in the spectra of the alkylation products, indicating the formation of compounds with structure 2.…”

mentioning

confidence: 99%

Alkylation of 3-aminoisocarbostyryl derivatives

Потиха

Gutsul²,

Ковтуненко

et al. 2011

Chem Heterocycl Comp

Self Cite

View full text Add to dashboard Cite

In this work, we continued our study of the chemical properties of uncondensed derivatives of 3-aminoisoquinolin-1(2H)-one (3-aminoisocarbostyryl) [1,2] and examined the reaction of alkyl halides with isocarbostyryls substituted at the 3-amino group. The alkylation of 3-aminoisocarbostyryls has been studied previously predominantly for condensed systems (reactions with alkyl halides [3-6] and dimethyl sulfate [7]). Only the 1,4-conjugate addition of olefins to 3-aminoisoquinolin-1(2H)-one has been described for uncondensed derivatives [8].Electrophilic substitution in 3-aminocarbostyryls, which are ambident nucleophiles, leads to different products depending both on the structure of the reagents and reaction conditions [3][4][5][6][7]. Thus, heating solutions of 3-(arylamino)isoquinolin-1(2H)-ones 1a-c and 3-(alkylamino)isoquinolin-1(2H)-ones 1d and 1e in acetonitrile with phenacyl bromide or alkyl halides (MeI, EtI, benzyl chloride) leads to a complex mixture of reaction products, which failed to be separated. The same result was obtained in an attempt to carry out the reaction by fusion of a mixture of reagents (with phenacyl bromide and benzyl chloride) or heating of the mixture in the presence of i-OPrNa in 2-propanol (according to mass-spectrometric and 1 H NMR spectral data).We have found that compounds 1a,b,d,e react with alkyl halides (MeI, EtI, and benzyl chloride) in DMF solution at room temperature in the presence of NaH and are converted into 3-(alkylanilino)isoquinolin-1(2H)-ones 2a and 2b and 3-(dialkylamino)isoquinolin-1(2H)-ones 2c-e.Isoquinolinones 2a-e were isolated from the reaction product mixtures as pure compounds and their structures were established using 1 H NMR spectroscopy (Tables 1-3).

show abstract

3-(Hetarylamino)- and 3-[(hetarylmethyl)amino]-isoquinolin-1(2H)-ones

Cited by 8 publications

References 18 publications

Condensed isoquinolines. 37.* Heterocyclization using 3-(arylamino)- and 3-(hetarylamino)isoquinolin-1(2H)-ones

Condensed isoquinolines. 37.* Heterocyclization using 3-(arylamino)- and 3-(hetarylamino)isoquinolin-1(2H)-ones

Photoredox-catalyzed coupling of acyl oxime acetates with thiophenols to give arylthioesters in water at room temperature

Alkylation of 3-aminoisocarbostyryl derivatives

Contact Info

Product

Resources

About