High yield synthesis of 4H-1,4-benzothiazine-1,1-dioxide derivatives

4H‐1,4‐Benzothiazine‐1,1‐dioxide derivatives were synthesized through a sequence of almost quantitative reactions. The commercial starting material 2‐(methylsulfanyl)aniline was Boc‐protected, N‐acylated and oxidized at the sulfur atom to obtain a sulfonyl derivative. An anionic transposition of the...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of heterocyclic chemistry 2008-09, Vol.45 (5), p.1445-1449
Hauptverfasser: De Montis, Stefania, Fattuoni, Claudia, Cadoni, Enzo, Cabiddu, Maria G., Usai, Michele, Cabiddu, Salvatore
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1449
container_issue 5
container_start_page 1445
container_title Journal of heterocyclic chemistry
container_volume 45
creator De Montis, Stefania
Fattuoni, Claudia
Cadoni, Enzo
Cabiddu, Maria G.
Usai, Michele
Cabiddu, Salvatore
description 4H‐1,4‐Benzothiazine‐1,1‐dioxide derivatives were synthesized through a sequence of almost quantitative reactions. The commercial starting material 2‐(methylsulfanyl)aniline was Boc‐protected, N‐acylated and oxidized at the sulfur atom to obtain a sulfonyl derivative. An anionic transposition of the acyl group followed by asimultaneous deprotection‐cyclization gave the title products in excellent yields. All products and intermediates were fully characterized.
doi_str_mv 10.1002/jhet.5570450530
format Article
fullrecord <record><control><sourceid>wiley_istex</sourceid><recordid>TN_cdi_wiley_primary_10_1002_jhet_5570450530_JHET5570450530</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>JHET5570450530</sourcerecordid><originalsourceid>FETCH-LOGICAL-i2450-42cf1df60d5b01460f295d019063c261a622ac87f29f3ded2e25f5f1b19198533</originalsourceid><addsrcrecordid>eNpFkE1PAjEQhhujiYieve4PsNjpxy6NJ0VkNUQPYCRemkKnbhHBbDfI8utdgpHT5H0zz2TyEHIJrAOM8et5gVVHqYxJxZRgR6QFWgqqQItj0mo2OAXFJ6fkLMZ5E0FkWYvc5-GjSOqAC5fEelkVGENMVj6ROYUrSae43K6qIthtWGLTAHVhtQkOE4dlWNsqrDGekxNvFxEv_mabvD70x72cDl8Gj73bIQ28eYpKPvPgfMqcmjKQKfNcK8dAs1TMeAo25dzOullTe-HQceTKKw9T0KC7Sog2udnf_QkLrM13Gb5sWRtgZmfA7AyYgwHzlPfHh9jQdE-HWOHmn7blp0kzkSnz9jwwXTl6v9OToRmJX7LXYBU</addsrcrecordid><sourcetype>Publisher</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>High yield synthesis of 4H-1,4-benzothiazine-1,1-dioxide derivatives</title><source>Wiley Online Library - AutoHoldings Journals</source><creator>De Montis, Stefania ; Fattuoni, Claudia ; Cadoni, Enzo ; Cabiddu, Maria G. ; Usai, Michele ; Cabiddu, Salvatore</creator><creatorcontrib>De Montis, Stefania ; Fattuoni, Claudia ; Cadoni, Enzo ; Cabiddu, Maria G. ; Usai, Michele ; Cabiddu, Salvatore</creatorcontrib><description>4H‐1,4‐Benzothiazine‐1,1‐dioxide derivatives were synthesized through a sequence of almost quantitative reactions. The commercial starting material 2‐(methylsulfanyl)aniline was Boc‐protected, N‐acylated and oxidized at the sulfur atom to obtain a sulfonyl derivative. An anionic transposition of the acyl group followed by asimultaneous deprotection‐cyclization gave the title products in excellent yields. All products and intermediates were fully characterized.</description><identifier>ISSN: 0022-152X</identifier><identifier>EISSN: 1943-5193</identifier><identifier>DOI: 10.1002/jhet.5570450530</identifier><language>eng</language><publisher>Hoboken: Wiley-Blackwell</publisher><ispartof>Journal of heterocyclic chemistry, 2008-09, Vol.45 (5), p.1445-1449</ispartof><rights>Copyright © 2008 Journal of Heterocyclic Chemistry</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fjhet.5570450530$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fjhet.5570450530$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>De Montis, Stefania</creatorcontrib><creatorcontrib>Fattuoni, Claudia</creatorcontrib><creatorcontrib>Cadoni, Enzo</creatorcontrib><creatorcontrib>Cabiddu, Maria G.</creatorcontrib><creatorcontrib>Usai, Michele</creatorcontrib><creatorcontrib>Cabiddu, Salvatore</creatorcontrib><title>High yield synthesis of 4H-1,4-benzothiazine-1,1-dioxide derivatives</title><title>Journal of heterocyclic chemistry</title><description>4H‐1,4‐Benzothiazine‐1,1‐dioxide derivatives were synthesized through a sequence of almost quantitative reactions. The commercial starting material 2‐(methylsulfanyl)aniline was Boc‐protected, N‐acylated and oxidized at the sulfur atom to obtain a sulfonyl derivative. An anionic transposition of the acyl group followed by asimultaneous deprotection‐cyclization gave the title products in excellent yields. All products and intermediates were fully characterized.</description><issn>0022-152X</issn><issn>1943-5193</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><recordid>eNpFkE1PAjEQhhujiYieve4PsNjpxy6NJ0VkNUQPYCRemkKnbhHBbDfI8utdgpHT5H0zz2TyEHIJrAOM8et5gVVHqYxJxZRgR6QFWgqqQItj0mo2OAXFJ6fkLMZ5E0FkWYvc5-GjSOqAC5fEelkVGENMVj6ROYUrSae43K6qIthtWGLTAHVhtQkOE4dlWNsqrDGekxNvFxEv_mabvD70x72cDl8Gj73bIQ28eYpKPvPgfMqcmjKQKfNcK8dAs1TMeAo25dzOullTe-HQceTKKw9T0KC7Sog2udnf_QkLrM13Gb5sWRtgZmfA7AyYgwHzlPfHh9jQdE-HWOHmn7blp0kzkSnz9jwwXTl6v9OToRmJX7LXYBU</recordid><startdate>200809</startdate><enddate>200809</enddate><creator>De Montis, Stefania</creator><creator>Fattuoni, Claudia</creator><creator>Cadoni, Enzo</creator><creator>Cabiddu, Maria G.</creator><creator>Usai, Michele</creator><creator>Cabiddu, Salvatore</creator><general>Wiley-Blackwell</general><general>Wiley‐Blackwell</general><scope>BSCLL</scope></search><sort><creationdate>200809</creationdate><title>High yield synthesis of 4H-1,4-benzothiazine-1,1-dioxide derivatives</title><author>De Montis, Stefania ; Fattuoni, Claudia ; Cadoni, Enzo ; Cabiddu, Maria G. ; Usai, Michele ; Cabiddu, Salvatore</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-i2450-42cf1df60d5b01460f295d019063c261a622ac87f29f3ded2e25f5f1b19198533</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>De Montis, Stefania</creatorcontrib><creatorcontrib>Fattuoni, Claudia</creatorcontrib><creatorcontrib>Cadoni, Enzo</creatorcontrib><creatorcontrib>Cabiddu, Maria G.</creatorcontrib><creatorcontrib>Usai, Michele</creatorcontrib><creatorcontrib>Cabiddu, Salvatore</creatorcontrib><collection>Istex</collection><jtitle>Journal of heterocyclic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>De Montis, Stefania</au><au>Fattuoni, Claudia</au><au>Cadoni, Enzo</au><au>Cabiddu, Maria G.</au><au>Usai, Michele</au><au>Cabiddu, Salvatore</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>High yield synthesis of 4H-1,4-benzothiazine-1,1-dioxide derivatives</atitle><jtitle>Journal of heterocyclic chemistry</jtitle><date>2008-09</date><risdate>2008</risdate><volume>45</volume><issue>5</issue><spage>1445</spage><epage>1449</epage><pages>1445-1449</pages><issn>0022-152X</issn><eissn>1943-5193</eissn><abstract>4H‐1,4‐Benzothiazine‐1,1‐dioxide derivatives were synthesized through a sequence of almost quantitative reactions. The commercial starting material 2‐(methylsulfanyl)aniline was Boc‐protected, N‐acylated and oxidized at the sulfur atom to obtain a sulfonyl derivative. An anionic transposition of the acyl group followed by asimultaneous deprotection‐cyclization gave the title products in excellent yields. All products and intermediates were fully characterized.</abstract><cop>Hoboken</cop><pub>Wiley-Blackwell</pub><doi>10.1002/jhet.5570450530</doi><tpages>5</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0022-152X
ispartof Journal of heterocyclic chemistry, 2008-09, Vol.45 (5), p.1445-1449
issn 0022-152X
1943-5193
language eng
recordid cdi_wiley_primary_10_1002_jhet_5570450530_JHET5570450530
source Wiley Online Library - AutoHoldings Journals
title High yield synthesis of 4H-1,4-benzothiazine-1,1-dioxide derivatives
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-01T09%3A49%3A57IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-wiley_istex&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=High%20yield%20synthesis%20of%204H-1,4-benzothiazine-1,1-dioxide%20derivatives&rft.jtitle=Journal%20of%20heterocyclic%20chemistry&rft.au=De%20Montis,%20Stefania&rft.date=2008-09&rft.volume=45&rft.issue=5&rft.spage=1445&rft.epage=1449&rft.pages=1445-1449&rft.issn=0022-152X&rft.eissn=1943-5193&rft_id=info:doi/10.1002/jhet.5570450530&rft_dat=%3Cwiley_istex%3EJHET5570450530%3C/wiley_istex%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true