Purines. LX. Dimroth Rearrangement and Concomitant Hydrolytic Deamination of 7-Alkyl-1-methyladenines
The Dimroth rearrangement of 7-alkyl-1-methyladenines (8) to produce 7-alkyl-N6-methyladenines (9) (63-72% yield) has been found to be accompanied with unusual hydrolytic deaminations to give 7-alkyl-1-methylhypoxanthines (10) (1-3.5%) and/or 7-alkylhypoxanthines (11) (12-22%), when effected in boil...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1994/02/15, Vol.42(2), pp.382-384 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | FUJII, Tozo SAITO, Tohru II, Ryoko SUZUKI, Tomoko |
| description | The Dimroth rearrangement of 7-alkyl-1-methyladenines (8) to produce 7-alkyl-N6-methyladenines (9) (63-72% yield) has been found to be accompanied with unusual hydrolytic deaminations to give 7-alkyl-1-methylhypoxanthines (10) (1-3.5%) and/or 7-alkylhypoxanthines (11) (12-22%), when effected in boiling H2O for 4-70 h. Probable pathways leading to these by-products are proposed. |
| doi_str_mv | 10.1248/cpb.42.382 |
| format | Article |
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LX. Dimroth Rearrangement and Concomitant Hydrolytic Deamination of 7-Alkyl-1-methyladenines</title><source>J-STAGE Free</source><source>EZB-FREE-00999 freely available EZB journals</source><source>Free Full-Text Journals in Chemistry</source><creator>FUJII, Tozo ; SAITO, Tohru ; II, Ryoko ; SUZUKI, Tomoko</creator><creatorcontrib>FUJII, Tozo ; SAITO, Tohru ; II, Ryoko ; SUZUKI, Tomoko</creatorcontrib><description>The Dimroth rearrangement of 7-alkyl-1-methyladenines (8) to produce 7-alkyl-N6-methyladenines (9) (63-72% yield) has been found to be accompanied with unusual hydrolytic deaminations to give 7-alkyl-1-methylhypoxanthines (10) (1-3.5%) and/or 7-alkylhypoxanthines (11) (12-22%), when effected in boiling H2O for 4-70 h. 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LX. Dimroth Rearrangement and Concomitant Hydrolytic Deamination of 7-Alkyl-1-methyladenines</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>The Dimroth rearrangement of 7-alkyl-1-methyladenines (8) to produce 7-alkyl-N6-methyladenines (9) (63-72% yield) has been found to be accompanied with unusual hydrolytic deaminations to give 7-alkyl-1-methylhypoxanthines (10) (1-3.5%) and/or 7-alkylhypoxanthines (11) (12-22%), when effected in boiling H2O for 4-70 h. Probable pathways leading to these by-products are proposed.</description><subject>adenine 1, 7-disubstituted</subject><subject>Chemistry</subject><subject>deamination hydrolytic</subject><subject>Dimroth rearrangement</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>hypoxanthine 1, 7-disubstituted</subject><subject>hypoxanthine 7-substituted</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>1994</creationdate><recordtype>article</recordtype><recordid>eNpdkF2L1DAUQIMoOK6--AsKig9Caz6b9HGZ1V1hQBEF38JtervTMU3GpPPQf2-GWVbYl4RwTw6XQ8hbRhvGpfnkjn0jeSMMf0Y2TEhdK87Fc7KhlHY1F614SV7lfKCUK6rFhuD3U5oC5qba_W6qm2lOcdlXPxBSgnCPM4algjBU2xhcnKcFyvtuHVL06zK56gZhngIsUwxVHCtdX_s_q69ZPeOyXz0MGM721-TFCD7jm4f7ivz68vnn9q7efbv9ur3e1U5xyeu-RwWM9oYPvRMKFZOUAtedNFwoPrZKwag0Oq1phzg62g_GUBg0GuZEL67Ih4v3mOLfE-bFzlN26D0EjKdsWWs6KnhbwHdPwEM8pVB2s0y2lLdSS1GojxfKpZhzwtEe0zRDWi2j9tzblt5Wclt6F_j9gxKyAz-Wfm7Kjz8kE5QbWbDtBTvkBe7xcQ6p9PR4NrJOmbOVX44i_z_dQ7IYxD_lKJcb</recordid><startdate>1994</startdate><enddate>1994</enddate><creator>FUJII, Tozo</creator><creator>SAITO, Tohru</creator><creator>II, Ryoko</creator><creator>SUZUKI, Tomoko</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>1994</creationdate><title>Purines. LX. Dimroth Rearrangement and Concomitant Hydrolytic Deamination of 7-Alkyl-1-methyladenines</title><author>FUJII, Tozo ; SAITO, Tohru ; II, Ryoko ; SUZUKI, Tomoko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5242-bbe5a10b82dbc35e51400a279482352f655af57ec7709eefc0bd880ad7e81c3b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1994</creationdate><topic>adenine 1, 7-disubstituted</topic><topic>Chemistry</topic><topic>deamination hydrolytic</topic><topic>Dimroth rearrangement</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>hypoxanthine 1, 7-disubstituted</topic><topic>hypoxanthine 7-substituted</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>FUJII, Tozo</creatorcontrib><creatorcontrib>SAITO, Tohru</creatorcontrib><creatorcontrib>II, Ryoko</creatorcontrib><creatorcontrib>SUZUKI, Tomoko</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>SAITO, Tohru</au><au>II, Ryoko</au><au>SUZUKI, Tomoko</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Purines. LX. Dimroth Rearrangement and Concomitant Hydrolytic Deamination of 7-Alkyl-1-methyladenines</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1994</date><risdate>1994</risdate><volume>42</volume><issue>2</issue><spage>382</spage><epage>384</epage><pages>382-384</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>The Dimroth rearrangement of 7-alkyl-1-methyladenines (8) to produce 7-alkyl-N6-methyladenines (9) (63-72% yield) has been found to be accompanied with unusual hydrolytic deaminations to give 7-alkyl-1-methylhypoxanthines (10) (1-3.5%) and/or 7-alkylhypoxanthines (11) (12-22%), when effected in boiling H2O for 4-70 h. Probable pathways leading to these by-products are proposed.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><doi>10.1248/cpb.42.382</doi><tpages>3</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Chemical and Pharmaceutical Bulletin, 1994/02/15, Vol.42(2), pp.382-384 |
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| language | eng |
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| source | J-STAGE Free; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | adenine 1, 7-disubstituted Chemistry deamination hydrolytic Dimroth rearrangement Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings hypoxanthine 1, 7-disubstituted hypoxanthine 7-substituted Organic chemistry Preparations and properties |
| title | Purines. LX. Dimroth Rearrangement and Concomitant Hydrolytic Deamination of 7-Alkyl-1-methyladenines |
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