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Synthesis and Some Reactions of 6H-Indolo[2,3-b]quinoxalines
6 H -Indolo[2,3- b ]quinoxalines were synthesized by condensation of isatin and 5-nitroisatin with o -phenylenediamine. The alkylation of the title compounds with dimethyl sulfate gave the corresponding quaternary salts which were converted to perchlorates and oxidized with potassium hexacyanoferrat...
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| Published in: | Russian journal of organic chemistry 2020-12, Vol.56 (12), p.2104-2108 |
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| Main Authors: | , |
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| Language: | English |
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| container_end_page | 2108 |
| container_issue | 12 |
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| container_title | Russian journal of organic chemistry |
| container_volume | 56 |
| creator | Shulga, S. I. Shulga, O. S. |
| description | 6
H
-Indolo[2,3-
b
]quinoxalines were synthesized by condensation of isatin and 5-nitroisatin with
o
-phenylenediamine. The alkylation of the title compounds with dimethyl sulfate gave the corresponding quaternary salts which were converted to perchlorates and oxidized with potassium hexacyanoferrate(III) to previously unknown 5-methyl-6
H
-indolo[2,3-
b
]quinoxalin-3-one and its 9-nitro derivative. Treatment of 6
H
-indolo[2,3-
b
]quinoxalin-3-ones with dimethyl sulfate afforded 3-methoxyindoloquinoxalinium salts which were demethylated by the action of hydrobromic acid at 130–140°C. The structure of the isolated compounds was confirmed by IR and NMR spectra and elemental analyses. |
| doi_str_mv | 10.1134/S107042802012009X |
| format | article |
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H
-Indolo[2,3-
b
]quinoxalines were synthesized by condensation of isatin and 5-nitroisatin with
o
-phenylenediamine. The alkylation of the title compounds with dimethyl sulfate gave the corresponding quaternary salts which were converted to perchlorates and oxidized with potassium hexacyanoferrate(III) to previously unknown 5-methyl-6
H
-indolo[2,3-
b
]quinoxalin-3-one and its 9-nitro derivative. Treatment of 6
H
-indolo[2,3-
b
]quinoxalin-3-ones with dimethyl sulfate afforded 3-methoxyindoloquinoxalinium salts which were demethylated by the action of hydrobromic acid at 130–140°C. The structure of the isolated compounds was confirmed by IR and NMR spectra and elemental analyses.</description><identifier>ISSN: 1070-4280</identifier><identifier>EISSN: 1608-3393</identifier><identifier>DOI: 10.1134/S107042802012009X</identifier><language>eng</language><publisher>Moscow: Pleiades Publishing</publisher><subject>Alkylation ; Chemical synthesis ; Chemistry ; Chemistry and Materials Science ; Dimethyl sulfate ; Hydrobromic acid ; NMR ; Nuclear magnetic resonance ; Organic Chemistry ; Perchlorates ; Phenylenediamine ; Potassium ferricyanide ; Quinoxalines</subject><ispartof>Russian journal of organic chemistry, 2020-12, Vol.56 (12), p.2104-2108</ispartof><rights>Pleiades Publishing, Ltd. 2020</rights><rights>Pleiades Publishing, Ltd. 2020.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c268t-937298499ef8750320507f004af984c921facb577c7138b6fc646e5c1ca523293</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Shulga, S. I.</creatorcontrib><creatorcontrib>Shulga, O. S.</creatorcontrib><title>Synthesis and Some Reactions of 6H-Indolo[2,3-b]quinoxalines</title><title>Russian journal of organic chemistry</title><addtitle>Russ J Org Chem</addtitle><description>6
H
-Indolo[2,3-
b
]quinoxalines were synthesized by condensation of isatin and 5-nitroisatin with
o
-phenylenediamine. The alkylation of the title compounds with dimethyl sulfate gave the corresponding quaternary salts which were converted to perchlorates and oxidized with potassium hexacyanoferrate(III) to previously unknown 5-methyl-6
H
-indolo[2,3-
b
]quinoxalin-3-one and its 9-nitro derivative. Treatment of 6
H
-indolo[2,3-
b
]quinoxalin-3-ones with dimethyl sulfate afforded 3-methoxyindoloquinoxalinium salts which were demethylated by the action of hydrobromic acid at 130–140°C. The structure of the isolated compounds was confirmed by IR and NMR spectra and elemental analyses.</description><subject>Alkylation</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Dimethyl sulfate</subject><subject>Hydrobromic acid</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organic Chemistry</subject><subject>Perchlorates</subject><subject>Phenylenediamine</subject><subject>Potassium ferricyanide</subject><subject>Quinoxalines</subject><issn>1070-4280</issn><issn>1608-3393</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp1UEtLAzEQDqJgrf4AbwtejU4emwd4kaK2UBCsgiCypGmiW9qkTbZg_70pFTyIpxnmew0fQucErghh_HpCQAKnCigQCqBfD1CPCFCYMc0Oy15gvMOP0UnOcwDghLMeuplsQ_fpcpsrE2bVJC5d9eSM7doYchV9JYZ4FGZxEd_oJcPT9_WmDfHLLNrg8ik68maR3dnP7KOX-7vnwRCPHx9Gg9sxtlSoDmsmqVZca-eVrIFRqEH68oHx5Ww1Jd7YaS2llYSpqfBWcOFqS6ypKaOa9dHF3neV4nrjctfM4yaFEtlQrgSRXCtRWGTPsinmnJxvVqldmrRtCDS7kpo_JRUN3Wty4YYPl36d_xd9A8m7Zec</recordid><startdate>20201201</startdate><enddate>20201201</enddate><creator>Shulga, S. I.</creator><creator>Shulga, O. S.</creator><general>Pleiades Publishing</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20201201</creationdate><title>Synthesis and Some Reactions of 6H-Indolo[2,3-b]quinoxalines</title><author>Shulga, S. I. ; Shulga, O. S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c268t-937298499ef8750320507f004af984c921facb577c7138b6fc646e5c1ca523293</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alkylation</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Dimethyl sulfate</topic><topic>Hydrobromic acid</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Organic Chemistry</topic><topic>Perchlorates</topic><topic>Phenylenediamine</topic><topic>Potassium ferricyanide</topic><topic>Quinoxalines</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shulga, S. I.</creatorcontrib><creatorcontrib>Shulga, O. S.</creatorcontrib><collection>CrossRef</collection><jtitle>Russian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shulga, S. I.</au><au>Shulga, O. S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Some Reactions of 6H-Indolo[2,3-b]quinoxalines</atitle><jtitle>Russian journal of organic chemistry</jtitle><stitle>Russ J Org Chem</stitle><date>2020-12-01</date><risdate>2020</risdate><volume>56</volume><issue>12</issue><spage>2104</spage><epage>2108</epage><pages>2104-2108</pages><issn>1070-4280</issn><eissn>1608-3393</eissn><abstract>6
H
-Indolo[2,3-
b
]quinoxalines were synthesized by condensation of isatin and 5-nitroisatin with
o
-phenylenediamine. The alkylation of the title compounds with dimethyl sulfate gave the corresponding quaternary salts which were converted to perchlorates and oxidized with potassium hexacyanoferrate(III) to previously unknown 5-methyl-6
H
-indolo[2,3-
b
]quinoxalin-3-one and its 9-nitro derivative. Treatment of 6
H
-indolo[2,3-
b
]quinoxalin-3-ones with dimethyl sulfate afforded 3-methoxyindoloquinoxalinium salts which were demethylated by the action of hydrobromic acid at 130–140°C. The structure of the isolated compounds was confirmed by IR and NMR spectra and elemental analyses.</abstract><cop>Moscow</cop><pub>Pleiades Publishing</pub><doi>10.1134/S107042802012009X</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1070-4280 |
| ispartof | Russian journal of organic chemistry, 2020-12, Vol.56 (12), p.2104-2108 |
| issn | 1070-4280 1608-3393 |
| language | eng |
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| source | Springer Link |
| subjects | Alkylation Chemical synthesis Chemistry Chemistry and Materials Science Dimethyl sulfate Hydrobromic acid NMR Nuclear magnetic resonance Organic Chemistry Perchlorates Phenylenediamine Potassium ferricyanide Quinoxalines |
| title | Synthesis and Some Reactions of 6H-Indolo[2,3-b]quinoxalines |
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