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Open chain nitrogen compounds. Part XIII. 1-Aryl-3-arylthiomethyl-3-methyltriazenes and 3-(arylazo)-1,3-thiazolidines
Reaction of 3-acetoxymethyl-1-aryl-3-methyltriazenes with sodium thiophenolate or thiocresolate in anhydrous dimethylformamide affords a new series of 3-arylthiomethyltriazenes ( 2 ), Ar-S-CH 2 -NMe-N=N-Ar′. These triazenes are remarkably labile in aqueous buffer and may be good pro-drugs for the ac...
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| Published in: | Canadian journal of chemistry 1988-10, Vol.66 (10), p.2487-2491 |
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| Main Authors: | , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c136f-5487eb65b4afa3da032b028b5cebd38035d452a455acf7e7996502a1ce58a0843 |
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| container_end_page | 2491 |
| container_issue | 10 |
| container_start_page | 2487 |
| container_title | Canadian journal of chemistry |
| container_volume | 66 |
| creator | Vaughan, Keith Manning, Hartford W Merrin, Marcus P Hooper, Donald L |
| description | Reaction of 3-acetoxymethyl-1-aryl-3-methyltriazenes with sodium thiophenolate or thiocresolate in anhydrous dimethylformamide affords a new series of 3-arylthiomethyltriazenes (
2
), Ar-S-CH
2
-NMe-N=N-Ar′. These triazenes are remarkably labile in aqueous buffer and may be good pro-drugs for the active metabolite of the antitumour dimethyltriazenes. The reaction of arenediazonium fluoroborates with 1,3-thiazolidine in aqueous acetone affords a new series of N-arylazo-1,3-thiazolidines (
4
); the arylazothiazolidines represent a new class of triazene in which the N3 nitrogen is incorporated into a heterocyclic unit, in this case a 1,3-thiazolidine. Nuclear magnetic resonance spectra of the arylazothiazolidines show evidence for rotational isomerism of the exocyclic N2N3 bond in the triazene moiety. |
| doi_str_mv | 10.1139/v88-391 |
| format | article |
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2
), Ar-S-CH
2
-NMe-N=N-Ar′. These triazenes are remarkably labile in aqueous buffer and may be good pro-drugs for the active metabolite of the antitumour dimethyltriazenes. The reaction of arenediazonium fluoroborates with 1,3-thiazolidine in aqueous acetone affords a new series of N-arylazo-1,3-thiazolidines (
4
); the arylazothiazolidines represent a new class of triazene in which the N3 nitrogen is incorporated into a heterocyclic unit, in this case a 1,3-thiazolidine. Nuclear magnetic resonance spectra of the arylazothiazolidines show evidence for rotational isomerism of the exocyclic N2N3 bond in the triazene moiety.</description><identifier>ISSN: 0008-4042</identifier><identifier>EISSN: 1480-3291</identifier><identifier>DOI: 10.1139/v88-391</identifier><language>eng</language><publisher>Ottawa, Canada: NRC Research Press</publisher><ispartof>Canadian journal of chemistry, 1988-10, Vol.66 (10), p.2487-2491</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c136f-5487eb65b4afa3da032b028b5cebd38035d452a455acf7e7996502a1ce58a0843</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Vaughan, Keith</creatorcontrib><creatorcontrib>Manning, Hartford W</creatorcontrib><creatorcontrib>Merrin, Marcus P</creatorcontrib><creatorcontrib>Hooper, Donald L</creatorcontrib><title>Open chain nitrogen compounds. Part XIII. 1-Aryl-3-arylthiomethyl-3-methyltriazenes and 3-(arylazo)-1,3-thiazolidines</title><title>Canadian journal of chemistry</title><addtitle>Revue canadienne de chimie</addtitle><description>Reaction of 3-acetoxymethyl-1-aryl-3-methyltriazenes with sodium thiophenolate or thiocresolate in anhydrous dimethylformamide affords a new series of 3-arylthiomethyltriazenes (
2
), Ar-S-CH
2
-NMe-N=N-Ar′. These triazenes are remarkably labile in aqueous buffer and may be good pro-drugs for the active metabolite of the antitumour dimethyltriazenes. The reaction of arenediazonium fluoroborates with 1,3-thiazolidine in aqueous acetone affords a new series of N-arylazo-1,3-thiazolidines (
4
); the arylazothiazolidines represent a new class of triazene in which the N3 nitrogen is incorporated into a heterocyclic unit, in this case a 1,3-thiazolidine. Nuclear magnetic resonance spectra of the arylazothiazolidines show evidence for rotational isomerism of the exocyclic N2N3 bond in the triazene moiety.</description><issn>0008-4042</issn><issn>1480-3291</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1988</creationdate><recordtype>article</recordtype><recordid>eNp9kEtLAzEUhYMoWKv4F2blC1Pz7GSWpfgYKNSFgrvhTpJxIm1mSKaC_fWm1q2uzjmX714uB6FzSiaU8uLuUynMC3qARlQogjkr6CEaEUIUFkSwY3QS40eKOWFyhDbL3vpMt-B85t0Quvdd7NZ9t_EmTrJnCEP2VpblJKN4Fr5WmGNIMrSuW9uh_RnszRAcbK23MQNvMo6vdhxsu2tMbzlOC8mvnHGJOEVHDayiPfvVMXp9uH-ZP-HF8rGczxZYUz5tsBQqt_VU1gIa4AYIZzVhqpba1oYrwqURkoGQEnST27woppIwoNpKBUQJPkaX-7s6dDEG21R9cOv0V0VJtWurSm1Vqa1E3uxJH3Sw0ULQ7T_wxd_wL1T1puHf0J94Tw</recordid><startdate>19881001</startdate><enddate>19881001</enddate><creator>Vaughan, Keith</creator><creator>Manning, Hartford W</creator><creator>Merrin, Marcus P</creator><creator>Hooper, Donald L</creator><general>NRC Research Press</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19881001</creationdate><title>Open chain nitrogen compounds. Part XIII. 1-Aryl-3-arylthiomethyl-3-methyltriazenes and 3-(arylazo)-1,3-thiazolidines</title><author>Vaughan, Keith ; Manning, Hartford W ; Merrin, Marcus P ; Hooper, Donald L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c136f-5487eb65b4afa3da032b028b5cebd38035d452a455acf7e7996502a1ce58a0843</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1988</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Vaughan, Keith</creatorcontrib><creatorcontrib>Manning, Hartford W</creatorcontrib><creatorcontrib>Merrin, Marcus P</creatorcontrib><creatorcontrib>Hooper, Donald L</creatorcontrib><collection>CrossRef</collection><jtitle>Canadian journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Vaughan, Keith</au><au>Manning, Hartford W</au><au>Merrin, Marcus P</au><au>Hooper, Donald L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Open chain nitrogen compounds. Part XIII. 1-Aryl-3-arylthiomethyl-3-methyltriazenes and 3-(arylazo)-1,3-thiazolidines</atitle><jtitle>Canadian journal of chemistry</jtitle><addtitle>Revue canadienne de chimie</addtitle><date>1988-10-01</date><risdate>1988</risdate><volume>66</volume><issue>10</issue><spage>2487</spage><epage>2491</epage><pages>2487-2491</pages><issn>0008-4042</issn><eissn>1480-3291</eissn><abstract>Reaction of 3-acetoxymethyl-1-aryl-3-methyltriazenes with sodium thiophenolate or thiocresolate in anhydrous dimethylformamide affords a new series of 3-arylthiomethyltriazenes (
2
), Ar-S-CH
2
-NMe-N=N-Ar′. These triazenes are remarkably labile in aqueous buffer and may be good pro-drugs for the active metabolite of the antitumour dimethyltriazenes. The reaction of arenediazonium fluoroborates with 1,3-thiazolidine in aqueous acetone affords a new series of N-arylazo-1,3-thiazolidines (
4
); the arylazothiazolidines represent a new class of triazene in which the N3 nitrogen is incorporated into a heterocyclic unit, in this case a 1,3-thiazolidine. Nuclear magnetic resonance spectra of the arylazothiazolidines show evidence for rotational isomerism of the exocyclic N2N3 bond in the triazene moiety.</abstract><cop>Ottawa, Canada</cop><pub>NRC Research Press</pub><doi>10.1139/v88-391</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0008-4042 |
| ispartof | Canadian journal of chemistry, 1988-10, Vol.66 (10), p.2487-2491 |
| issn | 0008-4042 1480-3291 |
| language | eng |
| recordid | cdi_crossref_primary_10_1139_v88_391 |
| source | EZB Electronic Journals Library |
| title | Open chain nitrogen compounds. Part XIII. 1-Aryl-3-arylthiomethyl-3-methyltriazenes and 3-(arylazo)-1,3-thiazolidines |
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