Loading…
A Microwave-Assisted Heck Reaction in Poly(ethylene glycol) for the Synthesis of Benzazepines
The Heck reaction of alkylated 2‐(trimethylsilyl)ethanesulfonyl (SES)‐protected β‐amino esters provides benzazepines in good yields. Good selectivity towards cyclisation was obtained when the reaction was performed in PEG 3400 as the solvent under microwave activation. Cleavage of the SES group with...
Saved in:
Published in: | European Journal of Organic Chemistry 2007-01, Vol.2007 (1), p.201-208 |
---|---|
Main Authors: | , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
cited_by | cdi_FETCH-LOGICAL-c3610-9f244dc5ce1257434f38d66a959689ac4f92b7720c7935802562fef59fd6ac433 |
---|---|
cites | cdi_FETCH-LOGICAL-c3610-9f244dc5ce1257434f38d66a959689ac4f92b7720c7935802562fef59fd6ac433 |
container_end_page | 208 |
container_issue | 1 |
container_start_page | 201 |
container_title | European Journal of Organic Chemistry |
container_volume | 2007 |
creator | Declerck, Valérie Ribière, Patrice Nédellec, Yannig Allouchi, Hassan Martinez, Jean Lamaty, Frédéric |
description | The Heck reaction of alkylated 2‐(trimethylsilyl)ethanesulfonyl (SES)‐protected β‐amino esters provides benzazepines in good yields. Good selectivity towards cyclisation was obtained when the reaction was performed in PEG 3400 as the solvent under microwave activation. Cleavage of the SES group with HF provides the corresponding free benzazepine. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007) |
doi_str_mv | 10.1002/ejoc.200600680 |
format | article |
fullrecord | <record><control><sourceid>istex_hal_p</sourceid><recordid>TN_cdi_hal_primary_oai_HAL_hal_00121002v1</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>ark_67375_WNG_G573GLJH_M</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3610-9f244dc5ce1257434f38d66a959689ac4f92b7720c7935802562fef59fd6ac433</originalsourceid><addsrcrecordid>eNqFkE1PAjEQhjdGExG9eu5RDovTdrdLj0gQJCDGj-jFNLVMZWHdJVsCLr_ebjDEm8kkM5l5n8nMGwSXFNoUgF3jojBtBiB8dOAoaFCQMgQh4djXEY9CKvnbaXDm3AIApBC0Ebx3ySQ1ZbHVGwy7zqVujTMyRLMkj6jNOi1ykubkociqK1zPqwxzJJ9ZZYqsRWxRkvUcyVOV--RZUlhyg_lO73CV5ujOgxOrM4cXv7kZvNz2n3vDcDwd3PW649BwQSGUlkXRzMQGKYsTf6nlnZkQWsZSdKQ2kZXsI0kYmETyuAMsFsyijaWdCT_lvBm09nvnOlOrMv3SZaUKnaphd6zqHgBltUkb6rXtvdZ_7VyJ9gBQULVG1Uaqg5EekHtgm2ZY_aNW_dG095cN92zt6_eB1eVSiYQnsXq9H6hBnPDBeDRUE_4D6WKFcA</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>A Microwave-Assisted Heck Reaction in Poly(ethylene glycol) for the Synthesis of Benzazepines</title><source>Wiley-Blackwell Read & Publish Collection</source><creator>Declerck, Valérie ; Ribière, Patrice ; Nédellec, Yannig ; Allouchi, Hassan ; Martinez, Jean ; Lamaty, Frédéric</creator><creatorcontrib>Declerck, Valérie ; Ribière, Patrice ; Nédellec, Yannig ; Allouchi, Hassan ; Martinez, Jean ; Lamaty, Frédéric</creatorcontrib><description>The Heck reaction of alkylated 2‐(trimethylsilyl)ethanesulfonyl (SES)‐protected β‐amino esters provides benzazepines in good yields. Good selectivity towards cyclisation was obtained when the reaction was performed in PEG 3400 as the solvent under microwave activation. Cleavage of the SES group with HF provides the corresponding free benzazepine. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.200600680</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Chemical Sciences ; Microwaves ; Nanoparticles ; Nitrogen heterocycles ; Organic chemistry ; Palladium ; Solvent effects</subject><ispartof>European Journal of Organic Chemistry, 2007-01, Vol.2007 (1), p.201-208</ispartof><rights>Copyright © 2007 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3610-9f244dc5ce1257434f38d66a959689ac4f92b7720c7935802562fef59fd6ac433</citedby><cites>FETCH-LOGICAL-c3610-9f244dc5ce1257434f38d66a959689ac4f92b7720c7935802562fef59fd6ac433</cites><orcidid>0000-0003-2213-9276</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,313,314,780,784,792,885,27922,27924,27925</link.rule.ids><backlink>$$Uhttps://hal.science/hal-00121002$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Declerck, Valérie</creatorcontrib><creatorcontrib>Ribière, Patrice</creatorcontrib><creatorcontrib>Nédellec, Yannig</creatorcontrib><creatorcontrib>Allouchi, Hassan</creatorcontrib><creatorcontrib>Martinez, Jean</creatorcontrib><creatorcontrib>Lamaty, Frédéric</creatorcontrib><title>A Microwave-Assisted Heck Reaction in Poly(ethylene glycol) for the Synthesis of Benzazepines</title><title>European Journal of Organic Chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>The Heck reaction of alkylated 2‐(trimethylsilyl)ethanesulfonyl (SES)‐protected β‐amino esters provides benzazepines in good yields. Good selectivity towards cyclisation was obtained when the reaction was performed in PEG 3400 as the solvent under microwave activation. Cleavage of the SES group with HF provides the corresponding free benzazepine. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)</description><subject>Chemical Sciences</subject><subject>Microwaves</subject><subject>Nanoparticles</subject><subject>Nitrogen heterocycles</subject><subject>Organic chemistry</subject><subject>Palladium</subject><subject>Solvent effects</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><recordid>eNqFkE1PAjEQhjdGExG9eu5RDovTdrdLj0gQJCDGj-jFNLVMZWHdJVsCLr_ebjDEm8kkM5l5n8nMGwSXFNoUgF3jojBtBiB8dOAoaFCQMgQh4djXEY9CKvnbaXDm3AIApBC0Ebx3ySQ1ZbHVGwy7zqVujTMyRLMkj6jNOi1ykubkociqK1zPqwxzJJ9ZZYqsRWxRkvUcyVOV--RZUlhyg_lO73CV5ujOgxOrM4cXv7kZvNz2n3vDcDwd3PW649BwQSGUlkXRzMQGKYsTf6nlnZkQWsZSdKQ2kZXsI0kYmETyuAMsFsyijaWdCT_lvBm09nvnOlOrMv3SZaUKnaphd6zqHgBltUkb6rXtvdZ_7VyJ9gBQULVG1Uaqg5EekHtgm2ZY_aNW_dG095cN92zt6_eB1eVSiYQnsXq9H6hBnPDBeDRUE_4D6WKFcA</recordid><startdate>200701</startdate><enddate>200701</enddate><creator>Declerck, Valérie</creator><creator>Ribière, Patrice</creator><creator>Nédellec, Yannig</creator><creator>Allouchi, Hassan</creator><creator>Martinez, Jean</creator><creator>Lamaty, Frédéric</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0003-2213-9276</orcidid></search><sort><creationdate>200701</creationdate><title>A Microwave-Assisted Heck Reaction in Poly(ethylene glycol) for the Synthesis of Benzazepines</title><author>Declerck, Valérie ; Ribière, Patrice ; Nédellec, Yannig ; Allouchi, Hassan ; Martinez, Jean ; Lamaty, Frédéric</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3610-9f244dc5ce1257434f38d66a959689ac4f92b7720c7935802562fef59fd6ac433</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Chemical Sciences</topic><topic>Microwaves</topic><topic>Nanoparticles</topic><topic>Nitrogen heterocycles</topic><topic>Organic chemistry</topic><topic>Palladium</topic><topic>Solvent effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Declerck, Valérie</creatorcontrib><creatorcontrib>Ribière, Patrice</creatorcontrib><creatorcontrib>Nédellec, Yannig</creatorcontrib><creatorcontrib>Allouchi, Hassan</creatorcontrib><creatorcontrib>Martinez, Jean</creatorcontrib><creatorcontrib>Lamaty, Frédéric</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>European Journal of Organic Chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Declerck, Valérie</au><au>Ribière, Patrice</au><au>Nédellec, Yannig</au><au>Allouchi, Hassan</au><au>Martinez, Jean</au><au>Lamaty, Frédéric</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Microwave-Assisted Heck Reaction in Poly(ethylene glycol) for the Synthesis of Benzazepines</atitle><jtitle>European Journal of Organic Chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2007-01</date><risdate>2007</risdate><volume>2007</volume><issue>1</issue><spage>201</spage><epage>208</epage><pages>201-208</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>The Heck reaction of alkylated 2‐(trimethylsilyl)ethanesulfonyl (SES)‐protected β‐amino esters provides benzazepines in good yields. Good selectivity towards cyclisation was obtained when the reaction was performed in PEG 3400 as the solvent under microwave activation. Cleavage of the SES group with HF provides the corresponding free benzazepine. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.200600680</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0003-2213-9276</orcidid></addata></record> |
fulltext | fulltext |
identifier | ISSN: 1434-193X |
ispartof | European Journal of Organic Chemistry, 2007-01, Vol.2007 (1), p.201-208 |
issn | 1434-193X 1099-0690 |
language | eng |
recordid | cdi_hal_primary_oai_HAL_hal_00121002v1 |
source | Wiley-Blackwell Read & Publish Collection |
subjects | Chemical Sciences Microwaves Nanoparticles Nitrogen heterocycles Organic chemistry Palladium Solvent effects |
title | A Microwave-Assisted Heck Reaction in Poly(ethylene glycol) for the Synthesis of Benzazepines |
url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-28T19%3A05%3A16IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-istex_hal_p&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=A%20Microwave-Assisted%20Heck%20Reaction%20in%20Poly(ethylene%20glycol)%20for%20the%20Synthesis%20of%20Benzazepines&rft.jtitle=European%20Journal%20of%20Organic%20Chemistry&rft.au=Declerck,%20Val%C3%A9rie&rft.date=2007-01&rft.volume=2007&rft.issue=1&rft.spage=201&rft.epage=208&rft.pages=201-208&rft.issn=1434-193X&rft.eissn=1099-0690&rft_id=info:doi/10.1002/ejoc.200600680&rft_dat=%3Cistex_hal_p%3Eark_67375_WNG_G573GLJH_M%3C/istex_hal_p%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c3610-9f244dc5ce1257434f38d66a959689ac4f92b7720c7935802562fef59fd6ac433%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true |