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Diastereoselective multi-component tandem condensation: synthesis of 2-amino-4-(2-furanone)-4-chromene-3-carbonitriles
A general strategy for a one-pot stereoselective synthesis of 2-amino-4-(2-furanone)-4 H -chromene-3-carbonitriles by reaction of salicylaldehyde, malononitrile and butenolides via a tandem Knoevenagel/Pinner/vinylogous Michael condensation is presented. The β,γ-butenolides gave a syn -selective MCR...
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| Published in: | Organic & biomolecular chemistry 2019-10, Vol.17 (39), p.8853-8857 |
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| container_end_page | 8857 |
| container_issue | 39 |
| container_start_page | 8853 |
| container_title | Organic & biomolecular chemistry |
| container_volume | 17 |
| creator | Gupta, Vijay Sahu, Debashish Jain, Shailja Vanka, Kumar Singh, Ravi P |
| description | A general strategy for a one-pot stereoselective synthesis of 2-amino-4-(2-furanone)-4
H
-chromene-3-carbonitriles by reaction of salicylaldehyde, malononitrile and butenolides
via
a tandem Knoevenagel/Pinner/vinylogous Michael condensation is presented. The β,γ-butenolides gave a
syn
-selective MCR adduct with a dr up to 11.5 : 1. The mechanistic insight into the MCR was obtained by DFT calculations.
Highly
syn
-selective unification of three components (salicylaldehyde, malononitrile and butenolides) in the presence of sodium
tert
-butoxide has been realised. The reaction proceeds
via
a tandem Knoevenagel/Pinner/vinylogous Michael condensation. |
| doi_str_mv | 10.1039/c9ob01345h |
| format | article |
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H
-chromene-3-carbonitriles by reaction of salicylaldehyde, malononitrile and butenolides
via
a tandem Knoevenagel/Pinner/vinylogous Michael condensation is presented. The β,γ-butenolides gave a
syn
-selective MCR adduct with a dr up to 11.5 : 1. The mechanistic insight into the MCR was obtained by DFT calculations.
Highly
syn
-selective unification of three components (salicylaldehyde, malononitrile and butenolides) in the presence of sodium
tert
-butoxide has been realised. The reaction proceeds
via
a tandem Knoevenagel/Pinner/vinylogous Michael condensation.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/c9ob01345h</identifier><ispartof>Organic & biomolecular chemistry, 2019-10, Vol.17 (39), p.8853-8857</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></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>Gupta, Vijay</creatorcontrib><creatorcontrib>Sahu, Debashish</creatorcontrib><creatorcontrib>Jain, Shailja</creatorcontrib><creatorcontrib>Vanka, Kumar</creatorcontrib><creatorcontrib>Singh, Ravi P</creatorcontrib><title>Diastereoselective multi-component tandem condensation: synthesis of 2-amino-4-(2-furanone)-4-chromene-3-carbonitriles</title><title>Organic & biomolecular chemistry</title><description>A general strategy for a one-pot stereoselective synthesis of 2-amino-4-(2-furanone)-4
H
-chromene-3-carbonitriles by reaction of salicylaldehyde, malononitrile and butenolides
via
a tandem Knoevenagel/Pinner/vinylogous Michael condensation is presented. The β,γ-butenolides gave a
syn
-selective MCR adduct with a dr up to 11.5 : 1. The mechanistic insight into the MCR was obtained by DFT calculations.
Highly
syn
-selective unification of three components (salicylaldehyde, malononitrile and butenolides) in the presence of sodium
tert
-butoxide has been realised. The reaction proceeds
via
a tandem Knoevenagel/Pinner/vinylogous Michael condensation.</description><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNqFjz1PAzEQRC0EEuGjoUdyCcUS-3zhdLRAxA-gjxxnT7fovBt5nUj591yBoKR6M3qaYoy58-7Ju9AvUy9b50O7Gs_MwrddB24V-vPf3LhLc6X65Zzvu-d2YY5vFLViQVGcMFU6os2HqRIkyXth5Gpr5B1mm2QGa6wk_GL1xHVEJbUy2AZiJhZo4aGB4VAiz8vHuaaxSEZGCJBi2QpTLTSh3piLIU6Ktz-8Nvfr98_XDyiaNvtCOZbT5u9M-M9_A9oATvM</recordid><startdate>20191009</startdate><enddate>20191009</enddate><creator>Gupta, Vijay</creator><creator>Sahu, Debashish</creator><creator>Jain, Shailja</creator><creator>Vanka, Kumar</creator><creator>Singh, Ravi P</creator><scope/></search><sort><creationdate>20191009</creationdate><title>Diastereoselective multi-component tandem condensation: synthesis of 2-amino-4-(2-furanone)-4-chromene-3-carbonitriles</title><author>Gupta, Vijay ; Sahu, Debashish ; Jain, Shailja ; Vanka, Kumar ; Singh, Ravi P</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-rsc_primary_c9ob01345h3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><creationdate>2019</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gupta, Vijay</creatorcontrib><creatorcontrib>Sahu, Debashish</creatorcontrib><creatorcontrib>Jain, Shailja</creatorcontrib><creatorcontrib>Vanka, Kumar</creatorcontrib><creatorcontrib>Singh, Ravi P</creatorcontrib><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gupta, Vijay</au><au>Sahu, Debashish</au><au>Jain, Shailja</au><au>Vanka, Kumar</au><au>Singh, Ravi P</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Diastereoselective multi-component tandem condensation: synthesis of 2-amino-4-(2-furanone)-4-chromene-3-carbonitriles</atitle><jtitle>Organic & biomolecular chemistry</jtitle><date>2019-10-09</date><risdate>2019</risdate><volume>17</volume><issue>39</issue><spage>8853</spage><epage>8857</epage><pages>8853-8857</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>A general strategy for a one-pot stereoselective synthesis of 2-amino-4-(2-furanone)-4
H
-chromene-3-carbonitriles by reaction of salicylaldehyde, malononitrile and butenolides
via
a tandem Knoevenagel/Pinner/vinylogous Michael condensation is presented. The β,γ-butenolides gave a
syn
-selective MCR adduct with a dr up to 11.5 : 1. The mechanistic insight into the MCR was obtained by DFT calculations.
Highly
syn
-selective unification of three components (salicylaldehyde, malononitrile and butenolides) in the presence of sodium
tert
-butoxide has been realised. The reaction proceeds
via
a tandem Knoevenagel/Pinner/vinylogous Michael condensation.</abstract><doi>10.1039/c9ob01345h</doi><tpages>5</tpages></addata></record> |
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| ispartof | Organic & biomolecular chemistry, 2019-10, Vol.17 (39), p.8853-8857 |
| issn | 1477-0520 1477-0539 |
| language | |
| recordid | cdi_rsc_primary_c9ob01345h |
| source | Royal Society of Chemistry |
| title | Diastereoselective multi-component tandem condensation: synthesis of 2-amino-4-(2-furanone)-4-chromene-3-carbonitriles |
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