Loading…

A highly facile approach to the synthesis of novel 2-(3-benzyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-N-phenylacetamides

A series of heterocyclic compounds were designed as potential nonnucleoside HIV reverse transcriptase inhibitors. Although the compounds ultimately proved inactive against HIV, during the course of the synthesis, a new and highly facile method to realize N-phenylacetamides was developed. Notably, th...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2013-02, Vol.54 (6), p.576-578
Main Authors: Novikov, Mikhail S., Babkov, Denis A., Paramonova, Maria P., Chizhov, Alexander O., Khandazhinskaya, Anastasia L., Seley-Radtke, Katherine L.
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-c463t-1712893f1e2e94414727b08813453fa082d8bb252ddf2c6224af2edd8b5ca5163
cites cdi_FETCH-LOGICAL-c463t-1712893f1e2e94414727b08813453fa082d8bb252ddf2c6224af2edd8b5ca5163
container_end_page 578
container_issue 6
container_start_page 576
container_title Tetrahedron letters
container_volume 54
creator Novikov, Mikhail S.
Babkov, Denis A.
Paramonova, Maria P.
Chizhov, Alexander O.
Khandazhinskaya, Anastasia L.
Seley-Radtke, Katherine L.
description A series of heterocyclic compounds were designed as potential nonnucleoside HIV reverse transcriptase inhibitors. Although the compounds ultimately proved inactive against HIV, during the course of the synthesis, a new and highly facile method to realize N-phenylacetamides was developed. Notably, the new route avoids the intractable workups and byproducts previously reported procedures have been associated with, thereby making this approach highly attractive to adaptation with other heterocyclics.
doi_str_mv 10.1016/j.tetlet.2012.11.090
format article
fullrecord <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_7111777</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0040403912020448</els_id><sourcerecordid>2390156067</sourcerecordid><originalsourceid>FETCH-LOGICAL-c463t-1712893f1e2e94414727b08813453fa082d8bb252ddf2c6224af2edd8b5ca5163</originalsourceid><addsrcrecordid>eNp9kV1rFDEUhoModq3-A5G5rLBZc5LM141QSv2Aojd6HTLJmU6W7GRMZpeO0P9ulq1Vb8zNIefjPW_yEPIa2AYYVO-2mxlnj_OGM-AbgA1r2ROygqYWVJQNPCUrxiSjkon2jLxIacvyqRr2nJwJzptaSrki95fF4G4HvxS9Ns5joacpBm2GYg7FPGCRljGH5FIR-mIMB_QFpxeCdjj-XDzla0mtC3eBwpqvRb5lV1EPi41hWqLbOetGCnTxb-kXOg04Ll4bnHUuYHpJnvXaJ3z1EM_J9w_X364-0ZuvHz9fXd5QIysxU6iBN63oATm2UoKsed2xpgEhS9Fr1nDbdB0vubU9NxXnUvccbU6WRpdQiXPy_qQ77bsdWoNj9ujVlP3puKignfq3MrpB3YaDqgGgrusscPEgEMOPPaZZ7Vwy6L0eMeyT4qJlUFasOrbKU6uJIaWI_eMaYOpITm3ViZw6klMAKpPLY2_-tvg49BvVnzdg_qiDw6iScTgatC6imZUN7v8bfgGp0qwI</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2390156067</pqid></control><display><type>article</type><title>A highly facile approach to the synthesis of novel 2-(3-benzyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-N-phenylacetamides</title><source>ScienceDirect Journals</source><creator>Novikov, Mikhail S. ; Babkov, Denis A. ; Paramonova, Maria P. ; Chizhov, Alexander O. ; Khandazhinskaya, Anastasia L. ; Seley-Radtke, Katherine L.</creator><creatorcontrib>Novikov, Mikhail S. ; Babkov, Denis A. ; Paramonova, Maria P. ; Chizhov, Alexander O. ; Khandazhinskaya, Anastasia L. ; Seley-Radtke, Katherine L.</creatorcontrib><description>A series of heterocyclic compounds were designed as potential nonnucleoside HIV reverse transcriptase inhibitors. Although the compounds ultimately proved inactive against HIV, during the course of the synthesis, a new and highly facile method to realize N-phenylacetamides was developed. Notably, the new route avoids the intractable workups and byproducts previously reported procedures have been associated with, thereby making this approach highly attractive to adaptation with other heterocyclics.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>EISSN: 0040-4039</identifier><identifier>DOI: 10.1016/j.tetlet.2012.11.090</identifier><identifier>PMID: 32287444</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Heteroaromatic ; Heterocycles ; NNRTI ; Pyrimidines</subject><ispartof>Tetrahedron letters, 2013-02, Vol.54 (6), p.576-578</ispartof><rights>2012 Elsevier Ltd</rights><rights>Copyright © 2012 Elsevier Ltd. All rights reserved.</rights><rights>Copyright © 2012 Elsevier Ltd. All rights reserved. 2012 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c463t-1712893f1e2e94414727b08813453fa082d8bb252ddf2c6224af2edd8b5ca5163</citedby><cites>FETCH-LOGICAL-c463t-1712893f1e2e94414727b08813453fa082d8bb252ddf2c6224af2edd8b5ca5163</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32287444$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Novikov, Mikhail S.</creatorcontrib><creatorcontrib>Babkov, Denis A.</creatorcontrib><creatorcontrib>Paramonova, Maria P.</creatorcontrib><creatorcontrib>Chizhov, Alexander O.</creatorcontrib><creatorcontrib>Khandazhinskaya, Anastasia L.</creatorcontrib><creatorcontrib>Seley-Radtke, Katherine L.</creatorcontrib><title>A highly facile approach to the synthesis of novel 2-(3-benzyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-N-phenylacetamides</title><title>Tetrahedron letters</title><addtitle>Tetrahedron Lett</addtitle><description>A series of heterocyclic compounds were designed as potential nonnucleoside HIV reverse transcriptase inhibitors. Although the compounds ultimately proved inactive against HIV, during the course of the synthesis, a new and highly facile method to realize N-phenylacetamides was developed. Notably, the new route avoids the intractable workups and byproducts previously reported procedures have been associated with, thereby making this approach highly attractive to adaptation with other heterocyclics.</description><subject>Heteroaromatic</subject><subject>Heterocycles</subject><subject>NNRTI</subject><subject>Pyrimidines</subject><issn>0040-4039</issn><issn>1873-3581</issn><issn>0040-4039</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNp9kV1rFDEUhoModq3-A5G5rLBZc5LM141QSv2Aojd6HTLJmU6W7GRMZpeO0P9ulq1Vb8zNIefjPW_yEPIa2AYYVO-2mxlnj_OGM-AbgA1r2ROygqYWVJQNPCUrxiSjkon2jLxIacvyqRr2nJwJzptaSrki95fF4G4HvxS9Ns5joacpBm2GYg7FPGCRljGH5FIR-mIMB_QFpxeCdjj-XDzla0mtC3eBwpqvRb5lV1EPi41hWqLbOetGCnTxb-kXOg04Ll4bnHUuYHpJnvXaJ3z1EM_J9w_X364-0ZuvHz9fXd5QIysxU6iBN63oATm2UoKsed2xpgEhS9Fr1nDbdB0vubU9NxXnUvccbU6WRpdQiXPy_qQ77bsdWoNj9ujVlP3puKignfq3MrpB3YaDqgGgrusscPEgEMOPPaZZ7Vwy6L0eMeyT4qJlUFasOrbKU6uJIaWI_eMaYOpITm3ViZw6klMAKpPLY2_-tvg49BvVnzdg_qiDw6iScTgatC6imZUN7v8bfgGp0qwI</recordid><startdate>20130206</startdate><enddate>20130206</enddate><creator>Novikov, Mikhail S.</creator><creator>Babkov, Denis A.</creator><creator>Paramonova, Maria P.</creator><creator>Chizhov, Alexander O.</creator><creator>Khandazhinskaya, Anastasia L.</creator><creator>Seley-Radtke, Katherine L.</creator><general>Elsevier Ltd</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20130206</creationdate><title>A highly facile approach to the synthesis of novel 2-(3-benzyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-N-phenylacetamides</title><author>Novikov, Mikhail S. ; Babkov, Denis A. ; Paramonova, Maria P. ; Chizhov, Alexander O. ; Khandazhinskaya, Anastasia L. ; Seley-Radtke, Katherine L.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c463t-1712893f1e2e94414727b08813453fa082d8bb252ddf2c6224af2edd8b5ca5163</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Heteroaromatic</topic><topic>Heterocycles</topic><topic>NNRTI</topic><topic>Pyrimidines</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Novikov, Mikhail S.</creatorcontrib><creatorcontrib>Babkov, Denis A.</creatorcontrib><creatorcontrib>Paramonova, Maria P.</creatorcontrib><creatorcontrib>Chizhov, Alexander O.</creatorcontrib><creatorcontrib>Khandazhinskaya, Anastasia L.</creatorcontrib><creatorcontrib>Seley-Radtke, Katherine L.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Novikov, Mikhail S.</au><au>Babkov, Denis A.</au><au>Paramonova, Maria P.</au><au>Chizhov, Alexander O.</au><au>Khandazhinskaya, Anastasia L.</au><au>Seley-Radtke, Katherine L.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A highly facile approach to the synthesis of novel 2-(3-benzyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-N-phenylacetamides</atitle><jtitle>Tetrahedron letters</jtitle><addtitle>Tetrahedron Lett</addtitle><date>2013-02-06</date><risdate>2013</risdate><volume>54</volume><issue>6</issue><spage>576</spage><epage>578</epage><pages>576-578</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><eissn>0040-4039</eissn><abstract>A series of heterocyclic compounds were designed as potential nonnucleoside HIV reverse transcriptase inhibitors. Although the compounds ultimately proved inactive against HIV, during the course of the synthesis, a new and highly facile method to realize N-phenylacetamides was developed. Notably, the new route avoids the intractable workups and byproducts previously reported procedures have been associated with, thereby making this approach highly attractive to adaptation with other heterocyclics.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>32287444</pmid><doi>10.1016/j.tetlet.2012.11.090</doi><tpages>3</tpages><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 0040-4039
ispartof Tetrahedron letters, 2013-02, Vol.54 (6), p.576-578
issn 0040-4039
1873-3581
0040-4039
language eng
recordid cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_7111777
source ScienceDirect Journals
subjects Heteroaromatic
Heterocycles
NNRTI
Pyrimidines
title A highly facile approach to the synthesis of novel 2-(3-benzyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-N-phenylacetamides
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-30T21%3A57%3A49IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=A%20highly%20facile%20approach%20to%20the%20synthesis%20of%20novel%202-(3-benzyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-N-phenylacetamides&rft.jtitle=Tetrahedron%20letters&rft.au=Novikov,%20Mikhail%20S.&rft.date=2013-02-06&rft.volume=54&rft.issue=6&rft.spage=576&rft.epage=578&rft.pages=576-578&rft.issn=0040-4039&rft.eissn=1873-3581&rft_id=info:doi/10.1016/j.tetlet.2012.11.090&rft_dat=%3Cproquest_pubme%3E2390156067%3C/proquest_pubme%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c463t-1712893f1e2e94414727b08813453fa082d8bb252ddf2c6224af2edd8b5ca5163%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2390156067&rft_id=info:pmid/32287444&rfr_iscdi=true