Reactions of N- and C-alkenylanilines: IX. Synthesis, oxidation, and nitration of some 7-methyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles

doi:10.1134/S1070428012070123

Paper

Reactions of N- and C-alkenylanilines: IX. Synthesis, oxidation, and nitration of some 7-methyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles

Published Aug 5, 2012 · D. A. Skladchikov, K. Y. Suponitskii, I. Abdrakhmanov

Russian Journal of Organic Chemistry

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Abstract

Heating of 4-acyl-3-iodo-7-methyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indoles in piperidine gave 4-acyl-7-methyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles which were oxidized with KMnO4 to obtain the corresponding 4-acyl-7-methyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole-1,2-diols. Oxidation of 4-acyl-7-methyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles at the olefinic double bond with hydrogen peroxide in acetonitrile in the presence of formic acid afforded stereoisomeric epoxides with cis and trans orientation of the nitrogen-containing and oxirane rings. Nitration with a mixture of ammonium nitrate and trifluoroacetic anhydride produced 5-nitro derivatives. The structure of 1-{(1aR*,1bR*,6bS*,7aS*)-5-methyl-1a,1b,2,6b,7,7ahexahydrooxireno[4,5]cyclopenta[1,2-b]indol-2-yl}ethanone was determined by X-ray analysis.

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This study demonstrates the synthesis, oxidation, and nitration of 7-methyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles, with potential applications in organic synthesis and drug discovery.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Reactions of N- and C-alkenylanilines: IX. Synthesis, oxidation, and nitration of some 7-methyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles

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References

Electronic hyperpolarizabilities for donor-acceptor molecules with long conjugated bridges: calculations versus experiment.

The M05-2X functional provides the best agreement to experiment for predicting molecular hyperpolarizabilities, making it a cost-effective tool for molecular nonlinear optical properties prediction.

Anion-induced conformational changes in 2,7-disubstituted indole-based receptors.

Anion-induced conformational changes in 2,7-disubstituted indole-based receptors favor the syn-syn conformation of C2 and C7 substituents, with interactions primarily occurring at the indole H1 proton.

Applicability of hybrid density functional theory methods to calculation of molecular hyperpolarizability.

Scaled BMK results provide the best agreement with experiment for predicting molecular hyperpolarizability in D/A-substituted benzenes and stilbenes, with semiquantitative accuracy needed for design.

Reactions of N- and C-alkenylanilines: VIII. Synthesis of functionalized cycloalka[b]indoles from o-(cycloalk-2-en-1-yl)anilines

N-acetyl-3-iodo1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole shows no isomerization, while N-acetyl-3-iodo1,2,3,3a,4,8b-hex

Aziridinyl quinone antitumor agents based on indoles and cyclopent[b]indoles: structure-activity relationships for cytotoxicity and antitumor activity.

Aziridinyl quinones with low DT-diaphorase substrate specificity and poor DNA alkylation show the lowest toxicity with the highest antitumor activity.

Citations

Axial Chiral Metal Complexes, Carbo- and Heterocycles: Modern Synthesis Strategies and Examples of the Effect of Atropoisomerism on the Structure of Reaction Products

Atropoisomerism in substrate molecules can control the induction of chiral sites in reactions, leading to novel metal complexes, carbo- and heterocycles, and atroposelective conversion of münchnones.

Chemical Utilization of Piperylene

Piperylene can be used to create biologically active compounds and valuable intermediates for the synthesis of nitrogen-containing heterocycles.

New atropoisomeric alkenylphenylglycine derivatives: Synthesis of (5R)- and (5S)-isomers of (1R,3aR,4S,11S)-3a,5,9,11-tetramethyl-4,5-dihydro-3aH-1,4-methano[1,3]oxazolo[3,2-a]quinolin-2-one

We synthesized new atropoisomeric alkenylphenylglycine derivatives, leading to compounds with a 4,5-dihydro-3aH-methano[1,3]oxazolo[3,2-a]quinolin-2-one structure.

Synthesis of 7-bromo, 7-phenylethynyl, 7-azido, and 7-nitro derivatives of N-acetyl-1,3a,4,8b-tetrahydrocyclopenta[b]indole

This study demonstrates the successful synthesis of 7-substituted N-acetyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles from anilines and 3-chlorocyclopentene, with no signal doubling observed in NMR

Synthesis of N-acetyl-3,3a,4,8b- and -1,3a,4,8b-tetrahydrocyclopenta[b]indoles from N- and 2-(cyclopent-2-en-1-yl)anilines

This study demonstrates the synthesis of N-acetyl-3,3a,4,8b- and -1,3a,4,8b-tetrahydrocyclopenta[b]indoles from N- and 2-(cyclopent-2-en-1-yl)anilines,

Reactions of N- and C-alkenylanilines: X. Synthesis of 2-vinyldihydroindoles from 4-methyl-2-(pent-3-en-2-yl)aniline

2-vinyldihydroindoles can be synthesized from 4-methyl-2-(pent-3-en-2-yl)aniline by reacting with pyridine, piperidine, N-alkylpiperidines, and dimethylformamide, yielding dehydrohalogenation

Reactions of N- and C-alkenylanilines: IX. Synthesis, oxidation, and nitration of some 7-methyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles

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References

Electronic hyperpolarizabilities for donor-acceptor molecules with long conjugated bridges: calculations versus experiment.

The M05-2X functional provides the best agreement to experiment for predicting molecular hyperpolarizabilities, making it a cost-effective tool for molecular nonlinear optical properties prediction.

Anion-induced conformational changes in 2,7-disubstituted indole-based receptors.

Anion-induced conformational changes in 2,7-disubstituted indole-based receptors favor the syn-syn conformation of C2 and C7 substituents, with interactions primarily occurring at the indole H1 proton.

Applicability of hybrid density functional theory methods to calculation of molecular hyperpolarizability.

Scaled BMK results provide the best agreement with experiment for predicting molecular hyperpolarizability in D/A-substituted benzenes and stilbenes, with semiquantitative accuracy needed for design.

Reactions of N- and C-alkenylanilines: VIII. Synthesis of functionalized cycloalka[b]indoles from o-(cycloalk-2-en-1-yl)anilines

N-acetyl-3-iodo1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole shows no isomerization, while N-acetyl-3-iodo1,2,3,3a,4,8b-hex

Aziridinyl quinone antitumor agents based on indoles and cyclopent[b]indoles: structure-activity relationships for cytotoxicity and antitumor activity.

Aziridinyl quinones with low DT-diaphorase substrate specificity and poor DNA alkylation show the lowest toxicity with the highest antitumor activity.

Citations

Axial Chiral Metal Complexes, Carbo- and Heterocycles: Modern Synthesis Strategies and Examples of the Effect of Atropoisomerism on the Structure of Reaction Products

Atropoisomerism in substrate molecules can control the induction of chiral sites in reactions, leading to novel metal complexes, carbo- and heterocycles, and atroposelective conversion of münchnones.

Chemical Utilization of Piperylene

Piperylene can be used to create biologically active compounds and valuable intermediates for the synthesis of nitrogen-containing heterocycles.

New atropoisomeric alkenylphenylglycine derivatives: Synthesis of (5R*)- and (5S*)-isomers of (1R*,3aR*,4S*,11S*)-3a,5,9,11-tetramethyl-4,5-dihydro-3aH-1,4-methano[1,3]oxazolo[3,2-a]quinolin-2-one

We synthesized new atropoisomeric alkenylphenylglycine derivatives, leading to compounds with a 4,5-dihydro-3aH-methano[1,3]oxazolo[3,2-a]quinolin-2-one structure.

Synthesis of 7-bromo, 7-phenylethynyl, 7-azido, and 7-nitro derivatives of N-acetyl-1,3a,4,8b-tetrahydrocyclopenta[b]indole

This study demonstrates the successful synthesis of 7-substituted N-acetyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles from anilines and 3-chlorocyclopentene, with no signal doubling observed in NMR

Synthesis of N-acetyl-3,3a,4,8b- and -1,3a,4,8b-tetrahydrocyclopenta[b]indoles from N- and 2-(cyclopent-2-en-1-yl)anilines

This study demonstrates the synthesis of N-acetyl-3,3a,4,8b- and -1,3a,4,8b-tetrahydrocyclopenta[b]indoles from N- and 2-(cyclopent-2-en-1-yl)anilines,

Reactions of N- and C-alkenylanilines: X. Synthesis of 2-vinyldihydroindoles from 4-methyl-2-(pent-3-en-2-yl)aniline

2-vinyldihydroindoles can be synthesized from 4-methyl-2-(pent-3-en-2-yl)aniline by reacting with pyridine, piperidine, N-alkylpiperidines, and dimethylformamide, yielding dehydrohalogenation

New atropoisomeric alkenylphenylglycine derivatives: Synthesis of (5R)- and (5S)-isomers of (1R,3aR,4S,11S)-3a,5,9,11-tetramethyl-4,5-dihydro-3aH-1,4-methano[1,3]oxazolo[3,2-a]quinolin-2-one