nN → πAr interactions stabilize the E-ac isomers of arylhydrazides and facilitate their SNAr autocyclizations

We describe a novel mechanism of stabilization of the E-ac isomer of an arylhydrazide via nN → π*Ar interactions. We further show that when a leaving group (F) is present at the ortho-position of the carbonyl group of such an arylhydrazide, the nN → π*Ar interaction facilitates an SNAr autocyclizati...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Chemical communications (Cambridge, England) England), 2021-10, Vol.57 (85), p.11236-11239
Hauptverfasser:	Jugal Kishore Rai Deka, Kalita, Debajit, Sahariah, Biswajit, Sarma, Bani Kanta
Format:	Artikel
Sprache:	eng
Schlagworte:	Biological activity Carbonyl groups Carbonyls Isomers Rings (mathematics)
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page	11239
container_issue	85
container_start_page	11236
container_title	Chemical communications (Cambridge, England)
container_volume	57
creator	Jugal Kishore Rai Deka Kalita, Debajit Sahariah, Biswajit Sarma, Bani Kanta
description	We describe a novel mechanism of stabilization of the E-ac isomer of an arylhydrazide via nN → πAr interactions. We further show that when a leaving group (F) is present at the ortho-position of the carbonyl group of such an arylhydrazide, the nN → πAr interaction facilitates an SNAr autocyclization reaction to produce indazolone, an important heterocycle with biological activity. Faster autocyclization of arylhydrazide is observed when an electron withdrawing group is present in the aryl ring, which is a characteristic of SNAr reactions.
doi_str_mv	10.1039/d1cc04533d
format	Article
fullrecord	<record><control><sourceid>proquest</sourceid><recordid>TN_cdi_proquest_miscellaneous_2580939541</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2585846889</sourcerecordid><originalsourceid>FETCH-LOGICAL-p611-aca3911928eedbedf92adedee1c7175b3f6676033fda4a4c0beccefe2b99e40a3</originalsourceid><addsrcrecordid>eNpdjrFOwzAQhi0EEqWw8ASWWFgCdmwn8VhVpSBVZaADW3WxL6qrNCm2M7QTEw_Ai_EOPAlpYeKW_4bvvv8IuebsjjOh7y03hkklhD0hAy4ymShZvJ4edqWTXEh1Ti5CWLN-uCoGZNvM6ffHJ_16H3nqmogeTHRtE2iIULra7ZHGFdJJAoa60G7QB9pWFPyuXu2sh72zGCg0llZgej5CPF44T1_mvRO62Jqd6UVw9F6SswrqgFd_OSSLh8li_JjMnqdP49Es2Wac92UgNOc6LRBtibbSKVi0iNzkPFelqLIsz5gQlQUJ0rASjcEK01JrlAzEkNz-are-feswxOXGBYN1DQ22XVimqmBaaCV5j978Q9dt55v-uQOlCpkVhRY_NextMw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2585846889</pqid></control><display><type>article</type><title>nN → πAr interactions stabilize the E-ac isomers of arylhydrazides and facilitate their SNAr autocyclizations</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Jugal Kishore Rai Deka ; Kalita, Debajit ; Sahariah, Biswajit ; Sarma, Bani Kanta</creator><creatorcontrib>Jugal Kishore Rai Deka ; Kalita, Debajit ; Sahariah, Biswajit ; Sarma, Bani Kanta</creatorcontrib><description>We describe a novel mechanism of stabilization of the E-ac isomer of an arylhydrazide via nN → πAr interactions. We further show that when a leaving group (F) is present at the ortho-position of the carbonyl group of such an arylhydrazide, the nN → πAr interaction facilitates an SNAr autocyclization reaction to produce indazolone, an important heterocycle with biological activity. Faster autocyclization of arylhydrazide is observed when an electron withdrawing group is present in the aryl ring, which is a characteristic of SNAr reactions.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d1cc04533d</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Biological activity ; Carbonyl groups ; Carbonyls ; Isomers ; Rings (mathematics)</subject><ispartof>Chemical communications (Cambridge, England), 2021-10, Vol.57 (85), p.11236-11239</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><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>314,777,781,27905,27906</link.rule.ids></links><search><creatorcontrib>Jugal Kishore Rai Deka</creatorcontrib><creatorcontrib>Kalita, Debajit</creatorcontrib><creatorcontrib>Sahariah, Biswajit</creatorcontrib><creatorcontrib>Sarma, Bani Kanta</creatorcontrib><title>nN → πAr interactions stabilize the E-ac isomers of arylhydrazides and facilitate their SNAr autocyclizations</title><title>Chemical communications (Cambridge, England)</title><description>We describe a novel mechanism of stabilization of the E-ac isomer of an arylhydrazide via nN → πAr interactions. We further show that when a leaving group (F) is present at the ortho-position of the carbonyl group of such an arylhydrazide, the nN → πAr interaction facilitates an SNAr autocyclization reaction to produce indazolone, an important heterocycle with biological activity. Faster autocyclization of arylhydrazide is observed when an electron withdrawing group is present in the aryl ring, which is a characteristic of SNAr reactions.</description><subject>Biological activity</subject><subject>Carbonyl groups</subject><subject>Carbonyls</subject><subject>Isomers</subject><subject>Rings (mathematics)</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpdjrFOwzAQhi0EEqWw8ASWWFgCdmwn8VhVpSBVZaADW3WxL6qrNCm2M7QTEw_Ai_EOPAlpYeKW_4bvvv8IuebsjjOh7y03hkklhD0hAy4ymShZvJ4edqWTXEh1Ti5CWLN-uCoGZNvM6ffHJ_16H3nqmogeTHRtE2iIULra7ZHGFdJJAoa60G7QB9pWFPyuXu2sh72zGCg0llZgej5CPF44T1_mvRO62Jqd6UVw9F6SswrqgFd_OSSLh8li_JjMnqdP49Es2Wac92UgNOc6LRBtibbSKVi0iNzkPFelqLIsz5gQlQUJ0rASjcEK01JrlAzEkNz-are-feswxOXGBYN1DQ22XVimqmBaaCV5j978Q9dt55v-uQOlCpkVhRY_NextMw</recordid><startdate>20211026</startdate><enddate>20211026</enddate><creator>Jugal Kishore Rai Deka</creator><creator>Kalita, Debajit</creator><creator>Sahariah, Biswajit</creator><creator>Sarma, Bani Kanta</creator><general>Royal Society of Chemistry</general><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope></search><sort><creationdate>20211026</creationdate><title>nN → πAr interactions stabilize the E-ac isomers of arylhydrazides and facilitate their SNAr autocyclizations</title><author>Jugal Kishore Rai Deka ; Kalita, Debajit ; Sahariah, Biswajit ; Sarma, Bani Kanta</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p611-aca3911928eedbedf92adedee1c7175b3f6676033fda4a4c0beccefe2b99e40a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Biological activity</topic><topic>Carbonyl groups</topic><topic>Carbonyls</topic><topic>Isomers</topic><topic>Rings (mathematics)</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jugal Kishore Rai Deka</creatorcontrib><creatorcontrib>Kalita, Debajit</creatorcontrib><creatorcontrib>Sahariah, Biswajit</creatorcontrib><creatorcontrib>Sarma, Bani Kanta</creatorcontrib><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><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jugal Kishore Rai Deka</au><au>Kalita, Debajit</au><au>Sahariah, Biswajit</au><au>Sarma, Bani Kanta</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>nN → πAr interactions stabilize the E-ac isomers of arylhydrazides and facilitate their SNAr autocyclizations</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><date>2021-10-26</date><risdate>2021</risdate><volume>57</volume><issue>85</issue><spage>11236</spage><epage>11239</epage><pages>11236-11239</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>We describe a novel mechanism of stabilization of the E-ac isomer of an arylhydrazide via nN → πAr interactions. We further show that when a leaving group (F) is present at the ortho-position of the carbonyl group of such an arylhydrazide, the nN → πAr interaction facilitates an SNAr autocyclization reaction to produce indazolone, an important heterocycle with biological activity. Faster autocyclization of arylhydrazide is observed when an electron withdrawing group is present in the aryl ring, which is a characteristic of SNAr reactions.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d1cc04533d</doi><tpages>4</tpages></addata></record>
fulltext	fulltext
identifier	ISSN: 1359-7345
ispartof	Chemical communications (Cambridge, England), 2021-10, Vol.57 (85), p.11236-11239
issn	1359-7345 1364-548X
language	eng
recordid	cdi_proquest_miscellaneous_2580939541
source	Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects	Biological activity Carbonyl groups Carbonyls Isomers Rings (mathematics)
title	nN → πAr interactions stabilize the E-ac isomers of arylhydrazides and facilitate their SNAr autocyclizations
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-18T08%3A45%3A49IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=nN%20%E2%86%92%20%CF%80Ar%20interactions%20stabilize%20the%20E-ac%20isomers%20of%20arylhydrazides%20and%20facilitate%20their%20SNAr%20autocyclizations&rft.jtitle=Chemical%20communications%20(Cambridge,%20England)&rft.au=Jugal%20Kishore%20Rai%20Deka&rft.date=2021-10-26&rft.volume=57&rft.issue=85&rft.spage=11236&rft.epage=11239&rft.pages=11236-11239&rft.issn=1359-7345&rft.eissn=1364-548X&rft_id=info:doi/10.1039/d1cc04533d&rft_dat=%3Cproquest%3E2585846889%3C/proquest%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2585846889&rft_id=info:pmid/&rfr_iscdi=true