Purines. LXXI. Preparation and Alkylation of 7-Alkyladenine 1-Oxides : A General Synthesis of 1-Alkoxy-7-alkyladenines
7-Methyladenine (6a) and 7-ethyladenine (6b) afforded the N(1)-oxides 7a, b in 78% yield each on treatment with m-chloroperoxybenzoic acid at room temperature; this is analogous to the previously reported N-oxidation of 7-benzyladenine (6c) to give the N(1)-oxide 7c. When treated with an excess of m...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1996/03/15, Vol.44(3), pp.594-598 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | ITAYA, Taisuke ITO, Nobuaki FUJII, Tozo |
| description | 7-Methyladenine (6a) and 7-ethyladenine (6b) afforded the N(1)-oxides 7a, b in 78% yield each on treatment with m-chloroperoxybenzoic acid at room temperature; this is analogous to the previously reported N-oxidation of 7-benzyladenine (6c) to give the N(1)-oxide 7c. When treated with an excess of methyl iodide, ethyl iodide, or benzyl bromide in N, N-dimethylacetamide at room temperature, each of the 1-oxides 7a-c underwent alkylation almost exculsively at the oxygen atom of the N-oxide group. The products, isolated in good yields, were the salts 8d-l·HX of the nine 1-alkoxy-7-alkyladenines, in which either the O-alkyl or the N(7)-alkyl group is any one of methyl, ethyl, and benzyl. The UV and 1H-NMR spectral data for 8·HX and some of their free bases 8 are presented. |
| doi_str_mv | 10.1248/cpb.44.594 |
| format | Article |
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LXXI. Preparation and Alkylation of 7-Alkyladenine 1-Oxides : A General Synthesis of 1-Alkoxy-7-alkyladenines</title><source>Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals</source><source>J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese</source><source>Free Full-Text Journals in Chemistry</source><creator>ITAYA, Taisuke ; ITO, Nobuaki ; FUJII, Tozo</creator><creatorcontrib>ITAYA, Taisuke ; ITO, Nobuaki ; FUJII, Tozo</creatorcontrib><description>7-Methyladenine (6a) and 7-ethyladenine (6b) afforded the N(1)-oxides 7a, b in 78% yield each on treatment with m-chloroperoxybenzoic acid at room temperature; this is analogous to the previously reported N-oxidation of 7-benzyladenine (6c) to give the N(1)-oxide 7c. When treated with an excess of methyl iodide, ethyl iodide, or benzyl bromide in N, N-dimethylacetamide at room temperature, each of the 1-oxides 7a-c underwent alkylation almost exculsively at the oxygen atom of the N-oxide group. The products, isolated in good yields, were the salts 8d-l·HX of the nine 1-alkoxy-7-alkyladenines, in which either the O-alkyl or the N(7)-alkyl group is any one of methyl, ethyl, and benzyl. The UV and 1H-NMR spectral data for 8·HX and some of their free bases 8 are presented.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.44.594</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>1-alkoxy-7-alkyladenine ; 1H-NMR ; 7-alkyladenine 1-oxide alkylation ; 7-alkyladenine N-oxidation ; Chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings ; Organic chemistry ; Preparations and properties</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1996/03/15, Vol.44(3), pp.594-598</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>1996 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4364-a9049bd6e4cefc8b23dcb28b7ee74fea87215cdfe4e57ca2dfead8073e2669753</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1883,4024,27923,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=3065913$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>ITAYA, Taisuke</creatorcontrib><creatorcontrib>ITO, Nobuaki</creatorcontrib><creatorcontrib>FUJII, Tozo</creatorcontrib><title>Purines. LXXI. Preparation and Alkylation of 7-Alkyladenine 1-Oxides : A General Synthesis of 1-Alkoxy-7-alkyladenines</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>7-Methyladenine (6a) and 7-ethyladenine (6b) afforded the N(1)-oxides 7a, b in 78% yield each on treatment with m-chloroperoxybenzoic acid at room temperature; this is analogous to the previously reported N-oxidation of 7-benzyladenine (6c) to give the N(1)-oxide 7c. When treated with an excess of methyl iodide, ethyl iodide, or benzyl bromide in N, N-dimethylacetamide at room temperature, each of the 1-oxides 7a-c underwent alkylation almost exculsively at the oxygen atom of the N-oxide group. The products, isolated in good yields, were the salts 8d-l·HX of the nine 1-alkoxy-7-alkyladenines, in which either the O-alkyl or the N(7)-alkyl group is any one of methyl, ethyl, and benzyl. The UV and 1H-NMR spectral data for 8·HX and some of their free bases 8 are presented.</description><subject>1-alkoxy-7-alkyladenine</subject><subject>1H-NMR</subject><subject>7-alkyladenine 1-oxide alkylation</subject><subject>7-alkyladenine N-oxidation</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1996</creationdate><recordtype>article</recordtype><recordid>eNpNkEtLw0AUhQdRsFY3_oJZuBImziuZxF0pWguFFlToLtxMbmxqTMJMlebfmxBRN_fBPd-Bewi5FjwQUsd3ts0CrYMw0SdkIpQ2LJRSnZIJ5zxhUkXqnFx4v-dchtyoCfnafLqyRh_Q1Xa7DOjGYQsODmVTU6hzOqveu2pcm4IaNu451j1EBVsfyxw9vaczusAaHVT0uasPO_SlHwAxAM2xY4bBP9JfkrMCKo9XP31KXh8fXuZPbLVeLOezFbNaRZpBwnWS5RFqi4WNM6lym8k4M4hGFwixkSK0eYEaQ2NB9hPkcf8YyihKTKim5Hb0ta7x3mGRtq78ANelgqdDYmmfWKp12ifWi29GcQveQlU4qG3pfwnFozARqpfNR9neH-ANf-_gDqWtcHAUSRgPrmosvfnfdQcuxVp9A-8bg8U</recordid><startdate>1996</startdate><enddate>1996</enddate><creator>ITAYA, Taisuke</creator><creator>ITO, Nobuaki</creator><creator>FUJII, Tozo</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>1996</creationdate><title>Purines. LXXI. Preparation and Alkylation of 7-Alkyladenine 1-Oxides : A General Synthesis of 1-Alkoxy-7-alkyladenines</title><author>ITAYA, Taisuke ; ITO, Nobuaki ; FUJII, Tozo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4364-a9049bd6e4cefc8b23dcb28b7ee74fea87215cdfe4e57ca2dfead8073e2669753</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1996</creationdate><topic>1-alkoxy-7-alkyladenine</topic><topic>1H-NMR</topic><topic>7-alkyladenine 1-oxide alkylation</topic><topic>7-alkyladenine N-oxidation</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>ITAYA, Taisuke</creatorcontrib><creatorcontrib>ITO, Nobuaki</creatorcontrib><creatorcontrib>FUJII, Tozo</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>ITAYA, Taisuke</au><au>ITO, Nobuaki</au><au>FUJII, Tozo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Purines. LXXI. Preparation and Alkylation of 7-Alkyladenine 1-Oxides : A General Synthesis of 1-Alkoxy-7-alkyladenines</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1996</date><risdate>1996</risdate><volume>44</volume><issue>3</issue><spage>594</spage><epage>598</epage><pages>594-598</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>7-Methyladenine (6a) and 7-ethyladenine (6b) afforded the N(1)-oxides 7a, b in 78% yield each on treatment with m-chloroperoxybenzoic acid at room temperature; this is analogous to the previously reported N-oxidation of 7-benzyladenine (6c) to give the N(1)-oxide 7c. When treated with an excess of methyl iodide, ethyl iodide, or benzyl bromide in N, N-dimethylacetamide at room temperature, each of the 1-oxides 7a-c underwent alkylation almost exculsively at the oxygen atom of the N-oxide group. The products, isolated in good yields, were the salts 8d-l·HX of the nine 1-alkoxy-7-alkyladenines, in which either the O-alkyl or the N(7)-alkyl group is any one of methyl, ethyl, and benzyl. The UV and 1H-NMR spectral data for 8·HX and some of their free bases 8 are presented.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><doi>10.1248/cpb.44.594</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Chemical and Pharmaceutical Bulletin, 1996/03/15, Vol.44(3), pp.594-598 |
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| source | Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese; Free Full-Text Journals in Chemistry |
| subjects | 1-alkoxy-7-alkyladenine 1H-NMR 7-alkyladenine 1-oxide alkylation 7-alkyladenine N-oxidation Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Organic chemistry Preparations and properties |
| title | Purines. LXXI. Preparation and Alkylation of 7-Alkyladenine 1-Oxides : A General Synthesis of 1-Alkoxy-7-alkyladenines |
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