Purines. LXIX. Direct N(1)-Oxidation of 7-Benzyladenine and Stepwise Syntheses of Its N(1)- and N(3)-Oxides
In contrast to the N(3)-selectivity in N-alkylation, N-oxidation of 7-benzyladenine (17) with m-chloroperoxybenzoic acid in MeOH has been found to give 7-benzyladenine 1-oxide (18) in 76% yield. Alternatively, the same N-oxide (18) has been synthesized in 81% yield from 1-benzyl-4-(ethoxymethyleneam...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1995/02/15, Vol.43(2), pp.328-331 |
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| creator | FUJII, Tozo OGAWA, Kazuo SAITO, Tohru ITAYA, Taisuke |
| description | In contrast to the N(3)-selectivity in N-alkylation, N-oxidation of 7-benzyladenine (17) with m-chloroperoxybenzoic acid in MeOH has been found to give 7-benzyladenine 1-oxide (18) in 76% yield. Alternatively, the same N-oxide (18) has been synthesized in 81% yield from 1-benzyl-4-(ethoxymethyleneamino)imidazole-5-carbonitrile(19) and hydroxylamine. Treatment of 1-benzyl-4-(hydroxyamino)imidazole-5-carbonitrile (24), obtained in 63% yield from the corresponding 4-nitro drivative (20) by catalytic hydrogenation (Pt/H2), with formamidine acetate in boiling EtOH furnished 7-benzyladenine 3-oxyde (23) in 78% yield. A UV spectroscopic approach indicated that the neutral species of 18 exists in H2O in the N(1)-oxide form rather than the N(1)-OH form (27). |
| doi_str_mv | 10.1248/cpb.43.328 |
| format | Article |
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LXIX. Direct N(1)-Oxidation of 7-Benzyladenine and Stepwise Syntheses of Its N(1)- and N(3)-Oxides</title><source>J-STAGE Free</source><source>Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals</source><source>Free Full-Text Journals in Chemistry</source><creator>FUJII, Tozo ; OGAWA, Kazuo ; SAITO, Tohru ; ITAYA, Taisuke</creator><creatorcontrib>FUJII, Tozo ; OGAWA, Kazuo ; SAITO, Tohru ; ITAYA, Taisuke</creatorcontrib><description>In contrast to the N(3)-selectivity in N-alkylation, N-oxidation of 7-benzyladenine (17) with m-chloroperoxybenzoic acid in MeOH has been found to give 7-benzyladenine 1-oxide (18) in 76% yield. Alternatively, the same N-oxide (18) has been synthesized in 81% yield from 1-benzyl-4-(ethoxymethyleneamino)imidazole-5-carbonitrile(19) and hydroxylamine. Treatment of 1-benzyl-4-(hydroxyamino)imidazole-5-carbonitrile (24), obtained in 63% yield from the corresponding 4-nitro drivative (20) by catalytic hydrogenation (Pt/H2), with formamidine acetate in boiling EtOH furnished 7-benzyladenine 3-oxyde (23) in 78% yield. A UV spectroscopic approach indicated that the neutral species of 18 exists in H2O in the N(1)-oxide form rather than the N(1)-OH form (27).</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.43.328</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>7-benzyladenine 1-oxide ; 7-benzyladenine 3-oxide ; 7-benzyladenine oxidation ; acid dissociation constant ; 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 ; m-chloroperoxybenzoic acid ; N-oxide tautomer ; Organic chemistry ; Preparations and properties</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1995/02/15, Vol.43(2), pp.328-331</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>1995 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 1995</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5248-8717a79c90bca62928a038cdb77056b294c13ce9a55d366e4d3016d8fcc6e3b03</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,1877,4010,27904,27905,27906</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=3501176$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>FUJII, Tozo</creatorcontrib><creatorcontrib>OGAWA, Kazuo</creatorcontrib><creatorcontrib>SAITO, Tohru</creatorcontrib><creatorcontrib>ITAYA, Taisuke</creatorcontrib><title>Purines. LXIX. Direct N(1)-Oxidation of 7-Benzyladenine and Stepwise Syntheses of Its N(1)- and N(3)-Oxides</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>In contrast to the N(3)-selectivity in N-alkylation, N-oxidation of 7-benzyladenine (17) with m-chloroperoxybenzoic acid in MeOH has been found to give 7-benzyladenine 1-oxide (18) in 76% yield. Alternatively, the same N-oxide (18) has been synthesized in 81% yield from 1-benzyl-4-(ethoxymethyleneamino)imidazole-5-carbonitrile(19) and hydroxylamine. Treatment of 1-benzyl-4-(hydroxyamino)imidazole-5-carbonitrile (24), obtained in 63% yield from the corresponding 4-nitro drivative (20) by catalytic hydrogenation (Pt/H2), with formamidine acetate in boiling EtOH furnished 7-benzyladenine 3-oxyde (23) in 78% yield. A UV spectroscopic approach indicated that the neutral species of 18 exists in H2O in the N(1)-oxide form rather than the N(1)-OH form (27).</description><subject>7-benzyladenine 1-oxide</subject><subject>7-benzyladenine 3-oxide</subject><subject>7-benzyladenine oxidation</subject><subject>acid dissociation constant</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>m-chloroperoxybenzoic acid</subject><subject>N-oxide tautomer</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>1995</creationdate><recordtype>article</recordtype><recordid>eNpdkF1rFDEUhoMouFZv_AUDilRhpvmYfMylrlUXllaoQu9CJnPGZp1m1pxZ7Prrm3VKC705uTjP-3DyEvKa0Yrx2pz4bVvVohLcPCELJmpdSs7FU7KglDYlF0o8Jy8QN5RySbVYkN_fdylEwKpYX64uq-JzSOCn4uyYvS_Pb0LnpjDGYuwLXX6C-G8_uA5iDhQudsXFBNu_AaG42MfpChDwQK4mnPP_mbNjMZsAX5JnvRsQXt29R-Tnl9Mfy2_l-vzravlxXXqZ_1AazbTTjW9o653iDTeOCuO7VmsqVcub2jPhoXFSdkIpqDtBmepM770C0VJxRN7N3m0a_-wAJ3sd0MMwuAjjDi2TUhvFmgy-eQRuxl2K-TbLakW5qg0zmfowUz6NiAl6u03h2qW9ZdQeWre5dVsLm1vP8Ns7pUPvhj656APeJ4SkjGmVseWMbXByv-B-79IU_AAHI2ukOVj5PLL8YXvlkoUobgEi6ZVI</recordid><startdate>1995</startdate><enddate>1995</enddate><creator>FUJII, Tozo</creator><creator>OGAWA, Kazuo</creator><creator>SAITO, Tohru</creator><creator>ITAYA, Taisuke</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><general>Japan Science and Technology Agency</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope></search><sort><creationdate>1995</creationdate><title>Purines. LXIX. Direct N(1)-Oxidation of 7-Benzyladenine and Stepwise Syntheses of Its N(1)- and N(3)-Oxides</title><author>FUJII, Tozo ; OGAWA, Kazuo ; SAITO, Tohru ; ITAYA, Taisuke</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5248-8717a79c90bca62928a038cdb77056b294c13ce9a55d366e4d3016d8fcc6e3b03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1995</creationdate><topic>7-benzyladenine 1-oxide</topic><topic>7-benzyladenine 3-oxide</topic><topic>7-benzyladenine oxidation</topic><topic>acid dissociation constant</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>m-chloroperoxybenzoic acid</topic><topic>N-oxide tautomer</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>FUJII, Tozo</creatorcontrib><creatorcontrib>OGAWA, Kazuo</creatorcontrib><creatorcontrib>SAITO, Tohru</creatorcontrib><creatorcontrib>ITAYA, Taisuke</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>FUJII, Tozo</au><au>OGAWA, Kazuo</au><au>SAITO, Tohru</au><au>ITAYA, Taisuke</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Purines. LXIX. Direct N(1)-Oxidation of 7-Benzyladenine and Stepwise Syntheses of Its N(1)- and N(3)-Oxides</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1995</date><risdate>1995</risdate><volume>43</volume><issue>2</issue><spage>328</spage><epage>331</epage><pages>328-331</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>In contrast to the N(3)-selectivity in N-alkylation, N-oxidation of 7-benzyladenine (17) with m-chloroperoxybenzoic acid in MeOH has been found to give 7-benzyladenine 1-oxide (18) in 76% yield. Alternatively, the same N-oxide (18) has been synthesized in 81% yield from 1-benzyl-4-(ethoxymethyleneamino)imidazole-5-carbonitrile(19) and hydroxylamine. Treatment of 1-benzyl-4-(hydroxyamino)imidazole-5-carbonitrile (24), obtained in 63% yield from the corresponding 4-nitro drivative (20) by catalytic hydrogenation (Pt/H2), with formamidine acetate in boiling EtOH furnished 7-benzyladenine 3-oxyde (23) in 78% yield. A UV spectroscopic approach indicated that the neutral species of 18 exists in H2O in the N(1)-oxide form rather than the N(1)-OH form (27).</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><doi>10.1248/cpb.43.328</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Chemical and Pharmaceutical Bulletin, 1995/02/15, Vol.43(2), pp.328-331 |
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| subjects | 7-benzyladenine 1-oxide 7-benzyladenine 3-oxide 7-benzyladenine oxidation acid dissociation constant 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 m-chloroperoxybenzoic acid N-oxide tautomer Organic chemistry Preparations and properties |
| title | Purines. LXIX. Direct N(1)-Oxidation of 7-Benzyladenine and Stepwise Syntheses of Its N(1)- and N(3)-Oxides |
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