Reactions of N-Aminopyrazoles with Halogenating Reagents and Synthesis of 1, 2, 3-Triazines
Reactions of N-aminopyrazoles with halogenating reagents (Cl2, Br2, I2, BrCl, ICl, IBr, N-chlorosuccinimide, and N-bromosuccinimide) were examined. Some of these reagents preferentially lead to oxidation of the amino group to give the corresponding 1, 2, 3-triazines as major products, while others m...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1988/10/25, Vol.36(10), pp.3838-3848 |
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| container_issue | 10 |
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| container_title | Chemical & pharmaceutical bulletin |
| container_volume | 36 |
| creator | OHSAWA, AKIO KAIHOH, TERUMITSU ITOH, TAKASHI OKADA, MAMIKO KAWABATA, CHIKAKO YAMAGUCHI, KENTARO IGETA, HIROSHI |
| description | Reactions of N-aminopyrazoles with halogenating reagents (Cl2, Br2, I2, BrCl, ICl, IBr, N-chlorosuccinimide, and N-bromosuccinimide) were examined. Some of these reagents preferentially lead to oxidation of the amino group to give the corresponding 1, 2, 3-triazines as major products, while others mainly gave either or both of 1-amino-4-halopyrazoles and 5-halo-1, 2, 3-triazines as the result of halogenation of the 4-position of the pyrazole ring prior to the oxidation of the amino group. In some cases, the oxidation of the amino group and the halogenation of the pyrazole ring proceeded concurrently to form not only the unhalogenated triazines but also the l -amino-4-halopyrazoles and the 5-halotriazines. Various reagents and reaction conditions were explored to utilize the reaction for the synthesis of halogenated and unhalogenated 1, 2, 3-triazines. |
| doi_str_mv | 10.1248/cpb.36.3838 |
| format | Article |
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Some of these reagents preferentially lead to oxidation of the amino group to give the corresponding 1, 2, 3-triazines as major products, while others mainly gave either or both of 1-amino-4-halopyrazoles and 5-halo-1, 2, 3-triazines as the result of halogenation of the 4-position of the pyrazole ring prior to the oxidation of the amino group. In some cases, the oxidation of the amino group and the halogenation of the pyrazole ring proceeded concurrently to form not only the unhalogenated triazines but also the l -amino-4-halopyrazoles and the 5-halotriazines. Various reagents and reaction conditions were explored to utilize the reaction for the synthesis of halogenated and unhalogenated 1, 2, 3-triazines.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.36.3838</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>1, 2, 3-triazine ; 1-aminohalopyrazole ; 1-aminopyrazole ; Chemistry ; Exact sciences and technology ; halo-1, 2, 3-triazine ; halogenation ; Heterocyclic compounds ; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings ; Organic chemistry ; oxidation ; Preparations and properties ; pyrazole ; ring expansion ; synthesis</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1988/10/25, Vol.36(10), pp.3838-3848</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>1990 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 1988</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c483t-d7f51ea45b00ac3fd2a81fb42f8611aa721ed1e6d9750db20a11f006d86b2c1c3</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=6585113$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>OHSAWA, AKIO</creatorcontrib><creatorcontrib>KAIHOH, TERUMITSU</creatorcontrib><creatorcontrib>ITOH, TAKASHI</creatorcontrib><creatorcontrib>OKADA, MAMIKO</creatorcontrib><creatorcontrib>KAWABATA, CHIKAKO</creatorcontrib><creatorcontrib>YAMAGUCHI, KENTARO</creatorcontrib><creatorcontrib>IGETA, HIROSHI</creatorcontrib><title>Reactions of N-Aminopyrazoles with Halogenating Reagents and Synthesis of 1, 2, 3-Triazines</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>Reactions of N-aminopyrazoles with halogenating reagents (Cl2, Br2, I2, BrCl, ICl, IBr, N-chlorosuccinimide, and N-bromosuccinimide) were examined. Some of these reagents preferentially lead to oxidation of the amino group to give the corresponding 1, 2, 3-triazines as major products, while others mainly gave either or both of 1-amino-4-halopyrazoles and 5-halo-1, 2, 3-triazines as the result of halogenation of the 4-position of the pyrazole ring prior to the oxidation of the amino group. In some cases, the oxidation of the amino group and the halogenation of the pyrazole ring proceeded concurrently to form not only the unhalogenated triazines but also the l -amino-4-halopyrazoles and the 5-halotriazines. Various reagents and reaction conditions were explored to utilize the reaction for the synthesis of halogenated and unhalogenated 1, 2, 3-triazines.</description><subject>1, 2, 3-triazine</subject><subject>1-aminohalopyrazole</subject><subject>1-aminopyrazole</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>halo-1, 2, 3-triazine</subject><subject>halogenation</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>oxidation</subject><subject>Preparations and properties</subject><subject>pyrazole</subject><subject>ring expansion</subject><subject>synthesis</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1988</creationdate><recordtype>article</recordtype><recordid>eNpFkE1rGzEQhkVJII6bU_6AoL3F62qkXa18NKZpCqGFfJxyELNaKZbZaF1JoTi_vnJtksvMwDzzDLyEXAKbA6_VN7Pt5kLOhRLqE5mAqNuq4VyckAljbFFxIcUZOU9pwxhvWCsm5OnOosl-DImOjv6qli8-jNtdxLdxsIn-9XlNb3AYn23A7MMzLXyZc6IYenq_C3ltk_9_DDPKZ1RUD9Hjmw82fSanDodkL459Sh6vvz-sbqrb3z9-rpa3lamVyFXfugYs1k3HGBrheo4KXFdzpyQAYsvB9mBlv2gb1necIYBjTPZKdtyAEVPy5eDdxvHPq01Zb8bXGMpLDbVkIEUrF4W6OlAmjilF6_Q2-heMOw1M79PTJT0tpN6nV-ivRycmg4OLGIxP7yeyUQ2AKNj1AdukXHJ532PM3gx2r4RFo_ba8uVYi_8DWGPUNoh_qKWG0A</recordid><startdate>1988</startdate><enddate>1988</enddate><creator>OHSAWA, AKIO</creator><creator>KAIHOH, TERUMITSU</creator><creator>ITOH, TAKASHI</creator><creator>OKADA, MAMIKO</creator><creator>KAWABATA, CHIKAKO</creator><creator>YAMAGUCHI, KENTARO</creator><creator>IGETA, HIROSHI</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>1988</creationdate><title>Reactions of N-Aminopyrazoles with Halogenating Reagents and Synthesis of 1, 2, 3-Triazines</title><author>OHSAWA, AKIO ; KAIHOH, TERUMITSU ; ITOH, TAKASHI ; OKADA, MAMIKO ; KAWABATA, CHIKAKO ; YAMAGUCHI, KENTARO ; IGETA, HIROSHI</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c483t-d7f51ea45b00ac3fd2a81fb42f8611aa721ed1e6d9750db20a11f006d86b2c1c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1988</creationdate><topic>1, 2, 3-triazine</topic><topic>1-aminohalopyrazole</topic><topic>1-aminopyrazole</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>halo-1, 2, 3-triazine</topic><topic>halogenation</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>oxidation</topic><topic>Preparations and properties</topic><topic>pyrazole</topic><topic>ring expansion</topic><topic>synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>OHSAWA, AKIO</creatorcontrib><creatorcontrib>KAIHOH, TERUMITSU</creatorcontrib><creatorcontrib>ITOH, TAKASHI</creatorcontrib><creatorcontrib>OKADA, MAMIKO</creatorcontrib><creatorcontrib>KAWABATA, CHIKAKO</creatorcontrib><creatorcontrib>YAMAGUCHI, KENTARO</creatorcontrib><creatorcontrib>IGETA, HIROSHI</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>OHSAWA, AKIO</au><au>KAIHOH, TERUMITSU</au><au>ITOH, TAKASHI</au><au>OKADA, MAMIKO</au><au>KAWABATA, CHIKAKO</au><au>YAMAGUCHI, KENTARO</au><au>IGETA, HIROSHI</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Reactions of N-Aminopyrazoles with Halogenating Reagents and Synthesis of 1, 2, 3-Triazines</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1988</date><risdate>1988</risdate><volume>36</volume><issue>10</issue><spage>3838</spage><epage>3848</epage><pages>3838-3848</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>Reactions of N-aminopyrazoles with halogenating reagents (Cl2, Br2, I2, BrCl, ICl, IBr, N-chlorosuccinimide, and N-bromosuccinimide) were examined. Some of these reagents preferentially lead to oxidation of the amino group to give the corresponding 1, 2, 3-triazines as major products, while others mainly gave either or both of 1-amino-4-halopyrazoles and 5-halo-1, 2, 3-triazines as the result of halogenation of the 4-position of the pyrazole ring prior to the oxidation of the amino group. In some cases, the oxidation of the amino group and the halogenation of the pyrazole ring proceeded concurrently to form not only the unhalogenated triazines but also the l -amino-4-halopyrazoles and the 5-halotriazines. Various reagents and reaction conditions were explored to utilize the reaction for the synthesis of halogenated and unhalogenated 1, 2, 3-triazines.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><doi>10.1248/cpb.36.3838</doi><tpages>11</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Chemical and Pharmaceutical Bulletin, 1988/10/25, Vol.36(10), pp.3838-3848 |
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| language | eng |
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| subjects | 1, 2, 3-triazine 1-aminohalopyrazole 1-aminopyrazole Chemistry Exact sciences and technology halo-1, 2, 3-triazine halogenation Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Organic chemistry oxidation Preparations and properties pyrazole ring expansion synthesis |
| title | Reactions of N-Aminopyrazoles with Halogenating Reagents and Synthesis of 1, 2, 3-Triazines |
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