Traceless Solid-Phase Synthesis of Trisubstituted Quinazolines
A traceless polymer-supported synthesis of 4-benzoylquinazolines was developed using the following commercially available building blocks: Fmoc-α-amino acids, 2-nitrobenzensulfonyl chlorides and α-bromoacetophenones. The acyclic intermediates underwent base-catalyzed rearrangement involving C–C and...
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| Veröffentlicht in: | ACS combinatorial science 2015-08, Vol.17 (8), p.470-473 |
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| container_title | ACS combinatorial science |
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| creator | Fülöpová, Veronika Cziesla, Lauren Fleming, Megan Lu, Yiwei Voelker, Adrienne Krchňák, Viktor |
| description | A traceless polymer-supported synthesis of 4-benzoylquinazolines was developed using the following commercially available building blocks: Fmoc-α-amino acids, 2-nitrobenzensulfonyl chlorides and α-bromoacetophenones. The acyclic intermediates underwent base-catalyzed rearrangement involving C–C and N–N bond formation followed by ring expansion and yielded resin-bound dihydroquinazoline-2-carboxylic acids. After they were released from the resin by treatment with trifluoroacetic acid, base-mediated decarboxylation produced the target quinazolines in moderate-to-high yields and purities. |
| doi_str_mv | 10.1021/acscombsci.5b00060 |
| format | Article |
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The acyclic intermediates underwent base-catalyzed rearrangement involving C–C and N–N bond formation followed by ring expansion and yielded resin-bound dihydroquinazoline-2-carboxylic acids. 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After they were released from the resin by treatment with trifluoroacetic acid, base-mediated decarboxylation produced the target quinazolines in moderate-to-high yields and purities.</description><subject>Acetophenones - chemistry</subject><subject>Amino acids</subject><subject>Amino Acids - chemistry</subject><subject>Bonding</subject><subject>Carbon-carbon composites</subject><subject>Chlorides</subject><subject>Combinatorial analysis</subject><subject>Decarboxylation</subject><subject>Fluorenes - chemistry</subject><subject>Molecular Structure</subject><subject>Nitrobenzenes - chemistry</subject><subject>Oxides</subject><subject>Quinazolines - chemical synthesis</subject><subject>Quinazolines - chemistry</subject><subject>Synthesis</subject><issn>2156-8952</issn><issn>2156-8944</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkE1LAzEQhoMottT-AQ-yRy9bk2yS3VwEKX5BQaX1HLLZhKbsR83sHuqvN6VVb-JpBuZ5X4YHoUuCZwRTcqMNmK4pwfgZLzHGAp-gMSVcpIVk7PRn53SEpgCbiGDGJBX4HI2oIIxTKsfodhW0sbUFSJZd7av0da3BJstd268teEg6l6yCh6GE3vdDb6vkbfCt_oxwa-ECnTldg50e5wS9P9yv5k_p4uXxeX63SHWW8z51VnJDaaY1lVZi7ojOqdYk50XOKsbKwmpnnOTCYLf_NF55gQkVLjeWyWyCrg-929B9DBZ61XiIf9e6td0AiuSC4lgmsn-gOKNZzmQRUXpATegAgnVqG3yjw04RrPaW1a9ldbQcQ1fH_qFsbPUT-XYagdkBiGG16YbQRjN_NX4B7gWJnA</recordid><startdate>20150810</startdate><enddate>20150810</enddate><creator>Fülöpová, Veronika</creator><creator>Cziesla, Lauren</creator><creator>Fleming, Megan</creator><creator>Lu, Yiwei</creator><creator>Voelker, Adrienne</creator><creator>Krchňák, Viktor</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20150810</creationdate><title>Traceless Solid-Phase Synthesis of Trisubstituted Quinazolines</title><author>Fülöpová, Veronika ; Cziesla, Lauren ; Fleming, Megan ; Lu, Yiwei ; Voelker, Adrienne ; Krchňák, Viktor</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a375t-fe95c223aa29e905f1a72aa175874d44b8eafcf956c0f000072a580126f7ce493</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Acetophenones - chemistry</topic><topic>Amino acids</topic><topic>Amino Acids - chemistry</topic><topic>Bonding</topic><topic>Carbon-carbon composites</topic><topic>Chlorides</topic><topic>Combinatorial analysis</topic><topic>Decarboxylation</topic><topic>Fluorenes - chemistry</topic><topic>Molecular Structure</topic><topic>Nitrobenzenes - chemistry</topic><topic>Oxides</topic><topic>Quinazolines - chemical synthesis</topic><topic>Quinazolines - chemistry</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fülöpová, Veronika</creatorcontrib><creatorcontrib>Cziesla, Lauren</creatorcontrib><creatorcontrib>Fleming, Megan</creatorcontrib><creatorcontrib>Lu, Yiwei</creatorcontrib><creatorcontrib>Voelker, Adrienne</creatorcontrib><creatorcontrib>Krchňák, Viktor</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>ACS combinatorial science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fülöpová, Veronika</au><au>Cziesla, Lauren</au><au>Fleming, Megan</au><au>Lu, Yiwei</au><au>Voelker, Adrienne</au><au>Krchňák, Viktor</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Traceless Solid-Phase Synthesis of Trisubstituted Quinazolines</atitle><jtitle>ACS combinatorial science</jtitle><addtitle>ACS Comb. 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| fulltext | fulltext |
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| ispartof | ACS combinatorial science, 2015-08, Vol.17 (8), p.470-473 |
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| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Acetophenones - chemistry Amino acids Amino Acids - chemistry Bonding Carbon-carbon composites Chlorides Combinatorial analysis Decarboxylation Fluorenes - chemistry Molecular Structure Nitrobenzenes - chemistry Oxides Quinazolines - chemical synthesis Quinazolines - chemistry Synthesis |
| title | Traceless Solid-Phase Synthesis of Trisubstituted Quinazolines |
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