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Mechanochemical synthesis of coumarins via Pechmann condensation under solvent-free conditions: an easy access to coumarins and annulated pyrano[2,3- f ] and [3,2- f ]indoles
A green protocol has been developed for the synthesis of simple coumarins and linear pyrano[2,3- f ] and [3,2- f ]indoles by the reaction of phenol derivatives with β-ketoesters under ball milling at ambient temperature in the presence of methanesulfonic acid as a mild acid catalyst. The significant...
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| Published in: | Green chemistry : an international journal and green chemistry resource : GC 2022-03, Vol.24 (6), p.2429-2437 |
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| Main Authors: | , , , , , , , |
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| Language: | English |
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| cites | cdi_FETCH-LOGICAL-c189t-f8c91f54f8bfb95cce6a3a5899905cd548e81259c1c2dab06914663355f4f1ea3 |
| container_end_page | 2437 |
| container_issue | 6 |
| container_start_page | 2429 |
| container_title | Green chemistry : an international journal and green chemistry resource : GC |
| container_volume | 24 |
| creator | Sharapov, Ainur D. Fatykhov, Ramil F. Khalymbadzha, Igor A. Sharutin, Vladimir V. Santra, Sougata Zyryanov, Grigory V. Chupakhin, Oleg N. Ranu, Brindaban C. |
| description | A green protocol has been developed for the synthesis of simple coumarins and linear pyrano[2,3-
f
] and [3,2-
f
]indoles by the reaction of phenol derivatives with β-ketoesters under ball milling at ambient temperature in the presence of methanesulfonic acid as a mild acid catalyst. The significant advantages of this procedure are high yields, scalability, no use of hazardous acids or solvents, shorter reaction time, ambient temperature, low cost, and straightforward purification without column chromatography. This procedure is associated with high EcoScale metrics and a low
E
-factor. In contrast to traditional Pechmann condensation procedures, the mechanochemical protocol leads to the synthesis of pyranoindoles with excellent regioselectivity and high yields. |
| doi_str_mv | 10.1039/D1GC04564D |
| format | article |
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f
] and [3,2-
f
]indoles by the reaction of phenol derivatives with β-ketoesters under ball milling at ambient temperature in the presence of methanesulfonic acid as a mild acid catalyst. The significant advantages of this procedure are high yields, scalability, no use of hazardous acids or solvents, shorter reaction time, ambient temperature, low cost, and straightforward purification without column chromatography. This procedure is associated with high EcoScale metrics and a low
E
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f
] and [3,2-
f
]indoles by the reaction of phenol derivatives with β-ketoesters under ball milling at ambient temperature in the presence of methanesulfonic acid as a mild acid catalyst. The significant advantages of this procedure are high yields, scalability, no use of hazardous acids or solvents, shorter reaction time, ambient temperature, low cost, and straightforward purification without column chromatography. This procedure is associated with high EcoScale metrics and a low
E
-factor. In contrast to traditional Pechmann condensation procedures, the mechanochemical protocol leads to the synthesis of pyranoindoles with excellent regioselectivity and high yields.</description><subject>Ambient temperature</subject><subject>Ball milling</subject><subject>Catalysts</subject><subject>Column chromatography</subject><subject>Green chemistry</subject><subject>Indoles</subject><subject>Ketoesters</subject><subject>Methanesulfonic acid</subject><subject>Phenols</subject><subject>Reaction time</subject><subject>Regioselectivity</subject><subject>Solvents</subject><subject>Synthesis</subject><issn>1463-9262</issn><issn>1463-9270</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpNUV1LwzAULaLgnL74CwK-yapJ06SNb7LpFCb6oE9DSpYmLKNLZm476J_yN5pNUR8u9-Mczv1KknOCrwim4npCpmOcM55PDpIByTlNRVbgw9-YZ8fJCcAKY0IKng-SzyetltJ5tdRrq2SDoHftUoMF5A1SvlvLYB2grZXoJVLX0rlYdrV2IFvrHepiHBD4Zqtdm5qg9R63OxBukHRIS-iRVEoDoNb_E5Wujua6Rra6Rps-xEHm2YimyKD3PTqno2yfWVf7RsNpcmRkA_rsxw-Tt_u71_FDOnuePo5vZ6kipYhTlEoQw3JTLsxCsNiaSypZKYTATNUsL3VJMiYUUVktF5iLeB9OKWMmN0RLOkwuvnU3wX90Gtpq5bvgYssq4zkWBSswj6zLb5YKHiBoU22Cjbv1FcHV7h_V3z_oF2Fyfzc</recordid><startdate>20220321</startdate><enddate>20220321</enddate><creator>Sharapov, Ainur D.</creator><creator>Fatykhov, Ramil F.</creator><creator>Khalymbadzha, Igor A.</creator><creator>Sharutin, Vladimir V.</creator><creator>Santra, Sougata</creator><creator>Zyryanov, Grigory V.</creator><creator>Chupakhin, Oleg N.</creator><creator>Ranu, Brindaban C.</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7ST</scope><scope>7U6</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>JG9</scope><orcidid>https://orcid.org/0000-0001-9020-1401</orcidid><orcidid>https://orcid.org/0000-0002-1672-2476</orcidid><orcidid>https://orcid.org/0000-0002-4186-6105</orcidid></search><sort><creationdate>20220321</creationdate><title>Mechanochemical synthesis of coumarins via Pechmann condensation under solvent-free conditions: an easy access to coumarins and annulated pyrano[2,3- f ] and [3,2- f ]indoles</title><author>Sharapov, Ainur D. ; Fatykhov, Ramil F. ; Khalymbadzha, Igor A. ; Sharutin, Vladimir V. ; Santra, Sougata ; Zyryanov, Grigory V. ; Chupakhin, Oleg N. ; Ranu, Brindaban C.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c189t-f8c91f54f8bfb95cce6a3a5899905cd548e81259c1c2dab06914663355f4f1ea3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Ambient temperature</topic><topic>Ball milling</topic><topic>Catalysts</topic><topic>Column chromatography</topic><topic>Green chemistry</topic><topic>Indoles</topic><topic>Ketoesters</topic><topic>Methanesulfonic acid</topic><topic>Phenols</topic><topic>Reaction time</topic><topic>Regioselectivity</topic><topic>Solvents</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sharapov, Ainur D.</creatorcontrib><creatorcontrib>Fatykhov, Ramil F.</creatorcontrib><creatorcontrib>Khalymbadzha, Igor A.</creatorcontrib><creatorcontrib>Sharutin, Vladimir V.</creatorcontrib><creatorcontrib>Santra, Sougata</creatorcontrib><creatorcontrib>Zyryanov, Grigory V.</creatorcontrib><creatorcontrib>Chupakhin, Oleg N.</creatorcontrib><creatorcontrib>Ranu, Brindaban C.</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Environment Abstracts</collection><collection>Sustainability Science Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Materials Research Database</collection><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sharapov, Ainur D.</au><au>Fatykhov, Ramil F.</au><au>Khalymbadzha, Igor A.</au><au>Sharutin, Vladimir V.</au><au>Santra, Sougata</au><au>Zyryanov, Grigory V.</au><au>Chupakhin, Oleg N.</au><au>Ranu, Brindaban C.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Mechanochemical synthesis of coumarins via Pechmann condensation under solvent-free conditions: an easy access to coumarins and annulated pyrano[2,3- f ] and [3,2- f ]indoles</atitle><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle><date>2022-03-21</date><risdate>2022</risdate><volume>24</volume><issue>6</issue><spage>2429</spage><epage>2437</epage><pages>2429-2437</pages><issn>1463-9262</issn><eissn>1463-9270</eissn><abstract>A green protocol has been developed for the synthesis of simple coumarins and linear pyrano[2,3-
f
] and [3,2-
f
]indoles by the reaction of phenol derivatives with β-ketoesters under ball milling at ambient temperature in the presence of methanesulfonic acid as a mild acid catalyst. The significant advantages of this procedure are high yields, scalability, no use of hazardous acids or solvents, shorter reaction time, ambient temperature, low cost, and straightforward purification without column chromatography. This procedure is associated with high EcoScale metrics and a low
E
-factor. In contrast to traditional Pechmann condensation procedures, the mechanochemical protocol leads to the synthesis of pyranoindoles with excellent regioselectivity and high yields.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/D1GC04564D</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0001-9020-1401</orcidid><orcidid>https://orcid.org/0000-0002-1672-2476</orcidid><orcidid>https://orcid.org/0000-0002-4186-6105</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1463-9262 |
| ispartof | Green chemistry : an international journal and green chemistry resource : GC, 2022-03, Vol.24 (6), p.2429-2437 |
| issn | 1463-9262 1463-9270 |
| language | eng |
| recordid | cdi_proquest_journals_2640975706 |
| source | Royal Society of Chemistry |
| subjects | Ambient temperature Ball milling Catalysts Column chromatography Green chemistry Indoles Ketoesters Methanesulfonic acid Phenols Reaction time Regioselectivity Solvents Synthesis |
| title | Mechanochemical synthesis of coumarins via Pechmann condensation under solvent-free conditions: an easy access to coumarins and annulated pyrano[2,3- f ] and [3,2- f ]indoles |
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