N-Bromosuccinimide as an oxidant for the transition-metal-free synthesis of 2-aminobenzoxazoles from benzoxazoles and secondary amines
A facile and transition-metal-free method was developed through merging the ring opening of benzoxazoles with secondary amines and N-bromosuccinimide (NBS) mediated oxidative cyclization toward the synthesis of 2-aminobenzoxazoles. NBS was selected as a powerful oxidant in the oxidative cyclization...
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Veröffentlicht in: | Organic & biomolecular chemistry 2014-05, Vol.12 (19), p.3108-3113 |
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container_title | Organic & biomolecular chemistry |
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creator | Wang, Xiaoe Xu, Daqian Miao, Chengxia Zhang, Qiaohong Sun, Wei |
description | A facile and transition-metal-free method was developed through merging the ring opening of benzoxazoles with secondary amines and N-bromosuccinimide (NBS) mediated oxidative cyclization toward the synthesis of 2-aminobenzoxazoles. NBS was selected as a powerful oxidant in the oxidative cyclization of ring-opening amidines to provide the desirable 2-aminobenzoxazoles in excellent yields (up to 94%). |
doi_str_mv | 10.1039/c4ob00386a |
format | Article |
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NBS was selected as a powerful oxidant in the oxidative cyclization of ring-opening amidines to provide the desirable 2-aminobenzoxazoles in excellent yields (up to 94%).</description><subject>Amination</subject><subject>Amines - chemistry</subject><subject>Benzoxazoles - chemical synthesis</subject><subject>Benzoxazoles - chemistry</subject><subject>Bromosuccinimide - chemistry</subject><subject>Catalysis</subject><subject>Cyclization</subject><subject>Oxidants - chemistry</subject><subject>Oxidation-Reduction</subject><subject>Receptors, Somatostatin - antagonists & inhibitors</subject><subject>Transition Elements - chemistry</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpVkN1KHjEQhkOp1J_2pBcgORRh62SzSTaH7Yc_BdETe7xkkwmN7CY2sx-oF-B1d0Wr9GiGmWcehpexrwK-CZD2xHdlBJC9dh_YnuiMaUBJ-_Gtb2GX7RPdAghrdPeJ7badAaWF3WNPV82PWuZCW-9TTnMKyB1xl3m5T8HlhcdS-fIb-VJdprSkkpsZFzc1sSJyesjrkhLxEnnbuDnlMmJ-LPfusUxIPK52_t_E5cAJfcnB1Qf-fIH0me1ENxF-ea0H7NfZ6c3morm8Pv-5-X7ZeKnk0riolexabTSa3nbKWy28AkCIOmjUKmBrRtP7Lniw0XS6taOKMUinoNdSHrCjF-9dLX-2SMswJ_I4TS5j2dIglDDS9gB2RY9fUF8LUcU43NU0ry8PAobn3If33Ff48NW7HWcMb-i_oOVfx4uAvg</recordid><startdate>20140521</startdate><enddate>20140521</enddate><creator>Wang, Xiaoe</creator><creator>Xu, Daqian</creator><creator>Miao, Chengxia</creator><creator>Zhang, Qiaohong</creator><creator>Sun, Wei</creator><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></search><sort><creationdate>20140521</creationdate><title>N-Bromosuccinimide as an oxidant for the transition-metal-free synthesis of 2-aminobenzoxazoles from benzoxazoles and secondary amines</title><author>Wang, Xiaoe ; Xu, Daqian ; Miao, Chengxia ; Zhang, Qiaohong ; Sun, Wei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c353t-af65342676e78945c961c500e0f6d6e65de27b78c4dc09f74629b5ffd3a508633</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Amination</topic><topic>Amines - chemistry</topic><topic>Benzoxazoles - chemical synthesis</topic><topic>Benzoxazoles - chemistry</topic><topic>Bromosuccinimide - chemistry</topic><topic>Catalysis</topic><topic>Cyclization</topic><topic>Oxidants - chemistry</topic><topic>Oxidation-Reduction</topic><topic>Receptors, Somatostatin - antagonists & inhibitors</topic><topic>Transition Elements - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Xiaoe</creatorcontrib><creatorcontrib>Xu, Daqian</creatorcontrib><creatorcontrib>Miao, Chengxia</creatorcontrib><creatorcontrib>Zhang, Qiaohong</creatorcontrib><creatorcontrib>Sun, Wei</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><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Xiaoe</au><au>Xu, Daqian</au><au>Miao, Chengxia</au><au>Zhang, Qiaohong</au><au>Sun, Wei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>N-Bromosuccinimide as an oxidant for the transition-metal-free synthesis of 2-aminobenzoxazoles from benzoxazoles and secondary amines</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2014-05-21</date><risdate>2014</risdate><volume>12</volume><issue>19</issue><spage>3108</spage><epage>3113</epage><pages>3108-3113</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>A facile and transition-metal-free method was developed through merging the ring opening of benzoxazoles with secondary amines and N-bromosuccinimide (NBS) mediated oxidative cyclization toward the synthesis of 2-aminobenzoxazoles. 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source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
subjects | Amination Amines - chemistry Benzoxazoles - chemical synthesis Benzoxazoles - chemistry Bromosuccinimide - chemistry Catalysis Cyclization Oxidants - chemistry Oxidation-Reduction Receptors, Somatostatin - antagonists & inhibitors Transition Elements - chemistry |
title | N-Bromosuccinimide as an oxidant for the transition-metal-free synthesis of 2-aminobenzoxazoles from benzoxazoles and secondary amines |
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