Iodine catalyzed one-pot synthesis of highly substituted N-methyl pyrroles via [3 + 2] annulation and their in vitro evaluation as antibacterial agentsElectronic supplementary information (ESI) available: All the 1H & 13C NMR and mass spectra of 4a-n are available. See DOI: 10.1039/c5ra11094g
A new class of highly substituted pyrroles have been synthesized via a simple, fast, and efficient method using environmentally friendly iodine catalyzed [3 + 2] annulation. N -Methyl- N -[( E )-1-(methylsulfanyl)-2-nitro-1-ethenyl]amine (NMSM) 1 and β-nitrostyrenes 3 underwent cycloaddition to affo...
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creator | Balachandra, Biguvu Shanmugam, Sivakumar Muneeswaran, Thillaichidambaram Ramakritinan, Muthiah |
description | A new class of highly substituted pyrroles have been synthesized
via
a simple, fast, and efficient method using environmentally friendly iodine catalyzed [3 + 2] annulation.
N
-Methyl-
N
-[(
E
)-1-(methylsulfanyl)-2-nitro-1-ethenyl]amine (NMSM)
1
and β-nitrostyrenes
3
underwent cycloaddition to afford the desired products
4
in excellent yields under solvent and metal free conditions. All the pyrrole derivatives were evaluated for their
in vitro
anti-bacterial activity. Among the synthesized pyrrole derivatives,
4b
,
4c
,
4e
,
4g
,
4i
,
4j
,
4l
,
4m
and
4n
displayed good inhibitory properties against a panel of Gram positive and negative infectious pathogens.
A new class of highly substituted pyrroles have been synthesized
via
a simple, fast, and efficient method using environmentally friendly iodine catalyzed [3 + 2] annulation. |
doi_str_mv | 10.1039/c5ra11094g |
format | Article |
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via
a simple, fast, and efficient method using environmentally friendly iodine catalyzed [3 + 2] annulation.
N
-Methyl-
N
-[(
E
)-1-(methylsulfanyl)-2-nitro-1-ethenyl]amine (NMSM)
1
and β-nitrostyrenes
3
underwent cycloaddition to afford the desired products
4
in excellent yields under solvent and metal free conditions. All the pyrrole derivatives were evaluated for their
in vitro
anti-bacterial activity. Among the synthesized pyrrole derivatives,
4b
,
4c
,
4e
,
4g
,
4i
,
4j
,
4l
,
4m
and
4n
displayed good inhibitory properties against a panel of Gram positive and negative infectious pathogens.
A new class of highly substituted pyrroles have been synthesized
via
a simple, fast, and efficient method using environmentally friendly iodine catalyzed [3 + 2] annulation.</description><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/c5ra11094g</identifier><language>eng</language><creationdate>2015-07</creationdate><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>Balachandra, Biguvu</creatorcontrib><creatorcontrib>Shanmugam, Sivakumar</creatorcontrib><creatorcontrib>Muneeswaran, Thillaichidambaram</creatorcontrib><creatorcontrib>Ramakritinan, Muthiah</creatorcontrib><title>Iodine catalyzed one-pot synthesis of highly substituted N-methyl pyrroles via [3 + 2] annulation and their in vitro evaluation as antibacterial agentsElectronic supplementary information (ESI) available: All the 1H & 13C NMR and mass spectra of 4a-n are available. See DOI: 10.1039/c5ra11094g</title><description>A new class of highly substituted pyrroles have been synthesized
via
a simple, fast, and efficient method using environmentally friendly iodine catalyzed [3 + 2] annulation.
N
-Methyl-
N
-[(
E
)-1-(methylsulfanyl)-2-nitro-1-ethenyl]amine (NMSM)
1
and β-nitrostyrenes
3
underwent cycloaddition to afford the desired products
4
in excellent yields under solvent and metal free conditions. All the pyrrole derivatives were evaluated for their
in vitro
anti-bacterial activity. Among the synthesized pyrrole derivatives,
4b
,
4c
,
4e
,
4g
,
4i
,
4j
,
4l
,
4m
and
4n
displayed good inhibitory properties against a panel of Gram positive and negative infectious pathogens.
A new class of highly substituted pyrroles have been synthesized
via
a simple, fast, and efficient method using environmentally friendly iodine catalyzed [3 + 2] annulation.</description><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNqFkEFLw0AQhaMgWLQX78J4UBRJzSZtoL1JrbQHK1hvImWaTJqVzW7Y2RTir3erhR4E3css8755b3eC4ExEPRElw7tsYFGIaNhfHwadOOqnYRylw-Ogy_wR-ZMORJyKzsHlzORSE2ToULWflIPRFNbGAbfalcSSwRRQynWpWuBmxU66xnluHlbkylZB3VprFDFsJMJbArcQvwNq3Sh00mh_zcE7SQtSe8ZZA7RB1exU9oCTK8wcWYkKcE3a8URR5kktMx9a14oq30Xbeo_C2Opn9nqymN0AblAqXCkawb1S2ygQU7gCkYxh_vTynV8hM3C99cTtf_oY-mhL--EeLIjg4Xk2gt87PA2OClRM3V09Cc4fJ6_jaWg5W9ZWVv5lyz2e_K9f_KUv67xIvgAF4ZLo</recordid><startdate>20150729</startdate><enddate>20150729</enddate><creator>Balachandra, Biguvu</creator><creator>Shanmugam, Sivakumar</creator><creator>Muneeswaran, Thillaichidambaram</creator><creator>Ramakritinan, Muthiah</creator><scope/></search><sort><creationdate>20150729</creationdate><title>Iodine catalyzed one-pot synthesis of highly substituted N-methyl pyrroles via [3 + 2] annulation and their in vitro evaluation as antibacterial agentsElectronic supplementary information (ESI) available: All the 1H & 13C NMR and mass spectra of 4a-n are available. See DOI: 10.1039/c5ra11094g</title><author>Balachandra, Biguvu ; Shanmugam, Sivakumar ; Muneeswaran, Thillaichidambaram ; Ramakritinan, Muthiah</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-rsc_primary_c5ra11094g3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Balachandra, Biguvu</creatorcontrib><creatorcontrib>Shanmugam, Sivakumar</creatorcontrib><creatorcontrib>Muneeswaran, Thillaichidambaram</creatorcontrib><creatorcontrib>Ramakritinan, Muthiah</creatorcontrib></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Balachandra, Biguvu</au><au>Shanmugam, Sivakumar</au><au>Muneeswaran, Thillaichidambaram</au><au>Ramakritinan, Muthiah</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Iodine catalyzed one-pot synthesis of highly substituted N-methyl pyrroles via [3 + 2] annulation and their in vitro evaluation as antibacterial agentsElectronic supplementary information (ESI) available: All the 1H & 13C NMR and mass spectra of 4a-n are available. See DOI: 10.1039/c5ra11094g</atitle><date>2015-07-29</date><risdate>2015</risdate><volume>5</volume><issue>79</issue><spage>64781</spage><epage>64789</epage><pages>64781-64789</pages><eissn>2046-2069</eissn><abstract>A new class of highly substituted pyrroles have been synthesized
via
a simple, fast, and efficient method using environmentally friendly iodine catalyzed [3 + 2] annulation.
N
-Methyl-
N
-[(
E
)-1-(methylsulfanyl)-2-nitro-1-ethenyl]amine (NMSM)
1
and β-nitrostyrenes
3
underwent cycloaddition to afford the desired products
4
in excellent yields under solvent and metal free conditions. All the pyrrole derivatives were evaluated for their
in vitro
anti-bacterial activity. Among the synthesized pyrrole derivatives,
4b
,
4c
,
4e
,
4g
,
4i
,
4j
,
4l
,
4m
and
4n
displayed good inhibitory properties against a panel of Gram positive and negative infectious pathogens.
A new class of highly substituted pyrroles have been synthesized
via
a simple, fast, and efficient method using environmentally friendly iodine catalyzed [3 + 2] annulation.</abstract><doi>10.1039/c5ra11094g</doi><tpages>9</tpages></addata></record> |
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source | Royal Society Of Chemistry Journals |
title | Iodine catalyzed one-pot synthesis of highly substituted N-methyl pyrroles via [3 + 2] annulation and their in vitro evaluation as antibacterial agentsElectronic supplementary information (ESI) available: All the 1H & 13C NMR and mass spectra of 4a-n are available. See DOI: 10.1039/c5ra11094g |
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