Mass-spectral behavior of nitrohydroxy- and nitromethoxymethylindoles

Терентьев, П. Б.; Khmel'nitskii, R. A.; Solov'ev, O. A.; Yudin, L. G.; Кост, А. Н.; Zinchenko, E. Ya.

doi:10.1007/bf00469863

Chem Heterocycl Compd

1978

DOI: 10.1007/bf00469863

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Mass-spectral behavior of nitrohydroxy- and nitromethoxymethylindoles

П. Б. Терентьев

R. A. Khmel'nitskii

O. A. Solov'ev

et al.

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Cited by 2 publications

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“…There are also low intensity peaks for the ions [M-15] + (9%) and [M-15-28] + (21%) which are typical of 7-OCH 3 substituted indoles [4]. The electronic spectra of compounds 3a,b agree well with the spectra of the analogs unmethylated at the nitrogen atom (R = H) [1].…”

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confidence: 68%

Synthesis of Functionally Substituted Pyrrolo[3,2-g]quinolines from 6-Amino-7-methoxy-1,2,3-trimethylindole

Yamashkin

Oreshkina

Romanova

et al. 2005

Chem Heterocycl Compd

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Keywords: 6-amino-7-methoxy-1,2,3-trimethylindole, acetylacetone, acetoacetic ester, dibenzoylmethane, functionally substituted pyrrolo[3,2-g]quinolines, trifluoroacetoacetic ester.Enamines prepared from 6-amino-2,3-dimethyl-7-methoxyindole (1a) and dicarbonyl compounds are converted to the corresponding pyrrolo[3,2-g]quinolines under acid conditions or via thermal cyclization [1]. Continuing our research in this area we have studied the behavior of 6-amino-7-methoxy-1,2,3-trimethylindole (1b) in reactions with the same β-dicarbonyl compounds and also with trifluoroacetoacetic ester.The result of the reaction of the aminoindole 1b with acetylacetone depends on the duration of the process. Hence refluxing compound 1b in excess acetylacetone over 1 h gives basically the enamino ketone 2a which contains traces of the pyrroloquinoline 3a. A more prolonged reflux (3 h) gives exclusively product 3a. It was unexpectedly found that the result of briefly (1.5 h) holding the aminoindole 1b with dibenzoylmethane at 180-185°C gave the corresponding pyrroloquinoline 3b immediately with an admixture of traces of the enamino ketone 2b. N R Me Me N H 2 OMe C H 2 O O R 1 R 2 N R Me Me N H OMe O R 2 R 1 N N R Me Me R 2 R 1 OMe + 1a,b 2a-c 3a,b 1a R = H; 1b, 2a-c, 3a R = Me; 2a, 3a R 1 = R 2 = Me; 2b, 3b R 1 = R 2 = Ph; 2c R 1 = Me, R 2 = OEt __________________________________________________________________________________________

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confidence: 68%

Synthesis of Functionally Substituted Pyrrolo[3,2-g]quinolines from 6-Amino-7-methoxy-1,2,3-trimethylindole

Yamashkin

Oreshkina

Romanova

et al. 2005

Chem Heterocycl Compd

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“…The formed molecular ion of the aminoindole 3 (with m/z 190) subsequently eliminates a Me radical and CO molecule which is typical of 5-methoxy-substituted indoles [3].…”

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confidence: 99%

The potential use of 6-amino-5-methoxy(methyl)-2,3-dimethyl-and 6-amino-5-methoxy(methyl)-1,2,3-trimethyl-indoles in the synthesis of pyrrolo[2,3-f]quinolines

Yamashkin

Oreshkina

Romanova

et al. 2006

Chem Heterocycl Compd

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β-dicarbonyl compounds has been studied. It was found that all of the amines investigated undergo condensation readily to form the corresponding enamines while the possible subsequent cyclization to give pyrrolo [2,3-f]quinolines was found only for the condensation product of 6-amino-2,3,5-trimethylindole with 4,4,4-trifluoroacetoacetic ester. Keywords:6-amino-5-methoxy-2,3-dimethylindole, 6-amino-5-methoxy-1,2,3-trimethylindole, 6-amino-1,2,3,5-tetramethylindole, 6-amino-2,3,5-trimethylindole, acetylacetone, acetoacetic ester, pyrrolo[2,3-f]quinoline, ethyl 4,4,4-trifluoroacetoacetate.Continuing our investigation of the development of targeted methods for the synthesis of substituted (including trifluoromethyl-containing) pyrroloquinolines (potential biologically active compounds) with specific ring conjugation [1] we have studied the reactions of 6-amino-2,3,5-trimethylindole (1), 6-amino-1,2,3,5-tetramethylindole (2), 6-amino-5-methoxy-2,3-dimethylindole (3), and 6-amino-5-methoxy-1,2,3-trimethylindole (4) with 4,4,4-trifluoroacetoacetic ester and other dicarbonyl compounds.Heating a mixture of the aminoindole 1 with trifluoroacetoacetic ester in benzene with a catalytic amount of glacial acetic acid gave a compound which had spectroscopic data corresponding to the structure 5. N R N H 2 Me Me R 1 CF 3 COCH 2 CO 2 Et N R Me Me R 1 N H O CF 3 OH N R Me Me R 1 N H O CF 3 OH + 1-4 5 6-8 1,5 R = Me, R 1 = H, 2,6 R = R 1 = Me, 3,7 R = OMe, R 1 = H, 4,8 R = OMe, R 1 = Me __________________________________________________________________________________________ 1 Mordovian N. P. Ogarev

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Mass-spectral behavior of nitrohydroxy- and nitromethoxymethylindoles

Cited by 2 publications

References 5 publications

Synthesis of Functionally Substituted Pyrrolo[3,2-g]quinolines from 6-Amino-7-methoxy-1,2,3-trimethylindole

Synthesis of Functionally Substituted Pyrrolo[3,2-g]quinolines from 6-Amino-7-methoxy-1,2,3-trimethylindole

The potential use of 6-amino-5-methoxy(methyl)-2,3-dimethyl-and 6-amino-5-methoxy(methyl)-1,2,3-trimethyl-indoles in the synthesis of pyrrolo[2,3-f]quinolines

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