{"id":11779,"date":"2022-12-02T03:56:09","date_gmt":"2022-12-01T19:56:09","guid":{"rendered":"https:\/\/www.pyrazoles-derivatives.com\/?p=11779"},"modified":"2022-12-02T03:56:09","modified_gmt":"2022-12-01T19:56:09","slug":"makisumi-yasuos-team-published-research-in-chemical-pharmaceutical-bulletin-in-10-cas-3553-12-6","status":"publish","type":"post","link":"https:\/\/www.pyrazoles-derivatives.com\/?p=11779","title":{"rendered":"Makisumi, Yasuo’s team published research in Chemical & Pharmaceutical Bulletin in 10 | CAS: 3553-12-6"},"content":{"rendered":"

Makisumi, Yasuo published the artcileAzaindolizine compounds. X. Synthesis of 5,7-disubstituted pyrazolo[1,5-a]pyrimidines<\/i><\/b>, Safety of 3-Acetamidopyrazole<\/a>, the publication is Chemical & Pharmaceutical Bulletin (1962), 612-20, database is CAplus.<\/p>\n

cf. CA 57, 16606b. The title compounds (I) were prepared in general by condensing AcCH2<\/sub>CO2<\/sub>Et (II), CH2<\/sub>Ac2<\/sub> (III), NCCH2<\/sub>CO2<\/sub>Et (IV), and CH2<\/sub>(CO2<\/sub>Et)2<\/sub> (V) separately with 5-amino-pyrazole (VI), its 1-Ph derivative (VII), its 4-EtO2<\/sub>C derivative (VIII), and its 4-NC. derivative (IX). II kept overnight at room temperature with VI, VII, or VIII in the absence of solvent gave the corresponding 5-EtO2<\/sub>CCH:CMeNH derivatives (X-XII) of pyrazole, m. 102\u00b0, 80-1\u00b0, and 175-6\u00b0, resp. On the other hand, refluxing II with VI or VIII 2-2.5 hrs. in AcOH gave the cyclized compounds (Ia, R = H and EtO2<\/sub>C), m. 298-9\u00b0 and 218-20\u00b0, resp., whereas refluxing II 4 hrs. with VII in AcOH gave the different cyclized compound (XIII), m. 188-9\u00b0. Ia (R = H and EtO2<\/sub>C) and XIII were formed also by refluxing X-XII 2-3 hrs. with AcOH. Ia (R = EtO2<\/sub>C) was also formed by refluxing XI 10 hrs. with Na in EtOH, and Ia (R = H) was prepared by refluxing VI 3 hrs. with II in EtOH containing anhydrous ZnCl2<\/sub>. Hydrolysis of 0.5 g. Ia (R = EtO2<\/sub>C) by heating 2 hrs. on a steam bath with 10% NaOH yielded 0.45 g. corresponding free acid, m. 296-7\u00b0 (decomposition), and this (0.5 g.) was successfully decarboxylated by refluxing 3 hrs. with 40% H2<\/sub>SO4<\/sub> to yield 0.32 g. Ia (R = H). Also, 0.94 g. IX refluxed 2.5 hrs. with II in AcOH yielded 1.5 g. Ia (R = cyano), m. 313\u00b0 (decomposition), and this (0.5 g.) hydrolyzed and decarboxylated by refluxing 4 hrs. with 40% H2<\/sub>SO4<\/sub> also yielded 0.4 g. Ia (R = H). Refluxing III (in place of II) with VI or VIII 10-12 hrs. in EtOH containing 3 drops piperidine, removing the solvent, and purifying the residue by Al2<\/sub>O3<\/sub> chromatography gave, resp., Ib (R = H), m. 40-40.5\u00b0, and Ib (R = EtO2<\/sub>C), m. 107-7.5\u00b0. The latter, like Ia (R = EtO2<\/sub>C) was hydrolyzed to the corresponding free acid, m. 178-9\u00b0, which was decarboxylated either by heating 20 min. at 200\u00b0 without solvent or by refluxing with 40% H2<\/sub>SO4<\/sub> to give Ib (R = H), formed likewise by refluxing the ester, Ib (R = EtO2<\/sub>C), itself with 40% H2<\/sub>SO4<\/sub>. Use of IV (in place of II or III) with VI or VIII in EtOH containing Na gave, resp., Ic (R = H), m. 306\u00b0 (decomposition), and Ic (R = EtO2<\/sub>C), m. 236-7\u00b0, which was hydrolyzed to the free acid, m. 296\u00b0 (decomposition), and this was decarboxylated by heating in vacuo at 260-70\u00b0 to give Ic (R = H). However, heating IV with VI 2 hrs. at 160-70\u00b0 in the absence of solvent gave the noncyclized 5-(2-cyanoacetamido)-pyrazole (XVI), m. 211-12\u00b0 (decomposition), and this was cyclized to Ic (R = H) by heating 5 hrs. on a steam bath in AcOH. Finally, V (in place of II) with VI or VIII in EtOH containing Na gave, resp., Id (R = H), m. 239-40\u00b0 (decomposition), and Id (R = EtO2<\/sub>C), m. 186-7\u00b0 (decomposition), which also was hydrolyzed to the corresponding acid, m. 229\u00b0 (decomposition), and this heated 5 min. at 235\u00b0 was not only decarboxylated but also decomposed to give 5-acetamidopyrazole (XV), m. 223-4\u00b0, identical with the product obtained by refluxing VI 1 hr. with AcOH. However, heating VI 15 min. on a steam bath with Ac2<\/sub>O gave 1-acetyl-5-acetamidopyrazole, m. 190.5-1.5\u00b0, which was readily converted to XV by heating with H2<\/sub>O. In support of the structures, ultraviolet absorption curves were shown for Ia (R = H, EtO2<\/sub>C, and CN), X-XII, Ic (R = H), Id (R = H), XIV, and XV, and both infrared and ultraviolet absorption data were reported for most of the compounds The infrared spectra of I showed that the 5- or 7-HO groups were mainly in the lactam form, whereas the 5- or 7-H2<\/sub>N groups kept the amino form in neutral medium, thus showing analogy with pyrimidine derivatives<\/p>\n

Chemical & Pharmaceutical Bulletin published new progress about 3553-12-6. 3553-12-6 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Amine,Amide, name is 3-Acetamidopyrazole, and the molecular formula is C5H7N3O, Safety of 3-Acetamidopyrazole<\/a>.<\/p>\n

Referemce:
https:\/\/en.wikipedia.org\/wiki\/Pyrazole<\/a>,
Pyrazoles – an overview | ScienceDirect Topics<\/a><\/p>\n","protected":false},"excerpt":{"rendered":"

Chemical & Pharmaceutical Bulletin published new progress about 3553-12-6. 3553-12-6 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Amine,Amide, name is 3-Acetamidopyrazole, and the molecular formula is C5H7N3O, Safety of 3-Acetamidopyrazole<\/a>.<\/p>\n","protected":false},"author":8,"featured_media":0,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[814,131],"tags":[732],"class_list":["post-11779","post","type-post","status-publish","format-standard","hentry","category-3553-12-6","category-pyrazoles-derivatives","tag-m-w100-150"],"yoast_head":"\nMakisumi, Yasuo's team published research in Chemical & Pharmaceutical Bulletin in 10 | CAS: 3553-12-6 | pyrazoles-derivatives<\/title>\n<meta name=\"description\" content=\"Makisumi, Yasuo published the artcileAzaindolizine compounds. X. Synthesis of 5,7-disubstituted pyrazolo[1,5-a]pyrimidines, Safety of 3-Acetamidopyrazole, the publication is Chemical & Pharmaceutical Bulletin (1962), 612-20, database is CAplus.\" \/>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.pyrazoles-derivatives.com\/?p=11779\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Makisumi, Yasuo's team published research in Chemical & Pharmaceutical Bulletin in 10 | CAS: 3553-12-6 | pyrazoles-derivatives\" \/>\n<meta property=\"og:description\" content=\"Makisumi, Yasuo published the artcileAzaindolizine compounds. X. Synthesis of 5,7-disubstituted pyrazolo[1,5-a]pyrimidines, Safety of 3-Acetamidopyrazole, the publication is Chemical & Pharmaceutical Bulletin (1962), 612-20, database is CAplus.\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.pyrazoles-derivatives.com\/?p=11779\" \/>\n<meta property=\"og:site_name\" content=\"pyrazoles-derivatives\" \/>\n<meta property=\"article:published_time\" content=\"2022-12-01T19:56:09+00:00\" \/>\n<meta name=\"author\" content=\"Jessica.F\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"Jessica.F\" \/>\n\t<meta name=\"twitter:label2\" content=\"Est. reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"3 minutes\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\/\/schema.org\",\"@graph\":[{\"@type\":\"WebPage\",\"@id\":\"https:\/\/www.pyrazoles-derivatives.com\/?p=11779\",\"url\":\"https:\/\/www.pyrazoles-derivatives.com\/?p=11779\",\"name\":\"Makisumi, Yasuo's team published research in Chemical & Pharmaceutical Bulletin in 10 | CAS: 3553-12-6 | pyrazoles-derivatives\",\"isPartOf\":{\"@id\":\"https:\/\/www.pyrazoles-derivatives.com\/#website\"},\"datePublished\":\"2022-12-01T19:56:09+00:00\",\"author\":{\"@id\":\"https:\/\/www.pyrazoles-derivatives.com\/#\/schema\/person\/d9a9f27bed675392c6f363a01ffd49f1\"},\"description\":\"Makisumi, Yasuo published the artcileAzaindolizine compounds. X. Synthesis of 5,7-disubstituted pyrazolo[1,5-a]pyrimidines, Safety of 3-Acetamidopyrazole, the publication is Chemical & Pharmaceutical Bulletin (1962), 612-20, database is CAplus.\",\"breadcrumb\":{\"@id\":\"https:\/\/www.pyrazoles-derivatives.com\/?p=11779#breadcrumb\"},\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"ReadAction\",\"target\":[\"https:\/\/www.pyrazoles-derivatives.com\/?p=11779\"]}]},{\"@type\":\"BreadcrumbList\",\"@id\":\"https:\/\/www.pyrazoles-derivatives.com\/?p=11779#breadcrumb\",\"itemListElement\":[{\"@type\":\"ListItem\",\"position\":1,\"name\":\"\u9996\u9875\",\"item\":\"https:\/\/www.pyrazoles-derivatives.com\/\"},{\"@type\":\"ListItem\",\"position\":2,\"name\":\"Makisumi, Yasuo’s team published research in Chemical & Pharmaceutical Bulletin in 10 | CAS: 3553-12-6\"}]},{\"@type\":\"WebSite\",\"@id\":\"https:\/\/www.pyrazoles-derivatives.com\/#website\",\"url\":\"https:\/\/www.pyrazoles-derivatives.com\/\",\"name\":\"pyrazoles-derivatives\",\"description\":\"Several pyrazole derivatives possess important pharmacological activities and they have been proved useful materials in drug research. Pyrazole derivatives play an important role in antitumor agents.\",\"potentialAction\":[{\"@type\":\"SearchAction\",\"target\":{\"@type\":\"EntryPoint\",\"urlTemplate\":\"https:\/\/www.pyrazoles-derivatives.com\/?s={search_term_string}\"},\"query-input\":{\"@type\":\"PropertyValueSpecification\",\"valueRequired\":true,\"valueName\":\"search_term_string\"}}],\"inLanguage\":\"en-US\"},{\"@type\":\"Person\",\"@id\":\"https:\/\/www.pyrazoles-derivatives.com\/#\/schema\/person\/d9a9f27bed675392c6f363a01ffd49f1\",\"name\":\"Jessica.F\",\"image\":{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\/\/www.pyrazoles-derivatives.com\/#\/schema\/person\/image\/\",\"url\":\"https:\/\/en.cravatar.com\/avatar\/2d1cec2a99eeaad5a5b217c9cdbfb610?s=96&d=mm&r=g\",\"contentUrl\":\"https:\/\/en.cravatar.com\/avatar\/2d1cec2a99eeaad5a5b217c9cdbfb610?s=96&d=mm&r=g\",\"caption\":\"Jessica.F\"}}]}<\/script>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"Makisumi, Yasuo's team published research in Chemical & Pharmaceutical Bulletin in 10 | CAS: 3553-12-6 | pyrazoles-derivatives","description":"Makisumi, Yasuo published the artcileAzaindolizine compounds. X. Synthesis of 5,7-disubstituted pyrazolo[1,5-a]pyrimidines, Safety of 3-Acetamidopyrazole, the publication is Chemical & Pharmaceutical Bulletin (1962), 612-20, database is CAplus.","robots":{"index":"index","follow":"follow","max-snippet":"max-snippet:-1","max-image-preview":"max-image-preview:large","max-video-preview":"max-video-preview:-1"},"canonical":"https:\/\/www.pyrazoles-derivatives.com\/?p=11779","og_locale":"en_US","og_type":"article","og_title":"Makisumi, Yasuo's team published research in Chemical & Pharmaceutical Bulletin in 10 | CAS: 3553-12-6 | pyrazoles-derivatives","og_description":"Makisumi, Yasuo published the artcileAzaindolizine compounds. X. Synthesis of 5,7-disubstituted pyrazolo[1,5-a]pyrimidines, Safety of 3-Acetamidopyrazole, the publication is Chemical & Pharmaceutical Bulletin (1962), 612-20, database is CAplus.","og_url":"https:\/\/www.pyrazoles-derivatives.com\/?p=11779","og_site_name":"pyrazoles-derivatives","article_published_time":"2022-12-01T19:56:09+00:00","author":"Jessica.F","twitter_card":"summary_large_image","twitter_misc":{"Written by":"Jessica.F","Est. reading time":"3 minutes"},"schema":{"@context":"https:\/\/schema.org","@graph":[{"@type":"WebPage","@id":"https:\/\/www.pyrazoles-derivatives.com\/?p=11779","url":"https:\/\/www.pyrazoles-derivatives.com\/?p=11779","name":"Makisumi, Yasuo's team published research in Chemical & Pharmaceutical Bulletin in 10 | CAS: 3553-12-6 | pyrazoles-derivatives","isPartOf":{"@id":"https:\/\/www.pyrazoles-derivatives.com\/#website"},"datePublished":"2022-12-01T19:56:09+00:00","author":{"@id":"https:\/\/www.pyrazoles-derivatives.com\/#\/schema\/person\/d9a9f27bed675392c6f363a01ffd49f1"},"description":"Makisumi, Yasuo published the artcileAzaindolizine compounds. X. Synthesis of 5,7-disubstituted pyrazolo[1,5-a]pyrimidines, Safety of 3-Acetamidopyrazole, the publication is Chemical & Pharmaceutical Bulletin (1962), 612-20, database is CAplus.","breadcrumb":{"@id":"https:\/\/www.pyrazoles-derivatives.com\/?p=11779#breadcrumb"},"inLanguage":"en-US","potentialAction":[{"@type":"ReadAction","target":["https:\/\/www.pyrazoles-derivatives.com\/?p=11779"]}]},{"@type":"BreadcrumbList","@id":"https:\/\/www.pyrazoles-derivatives.com\/?p=11779#breadcrumb","itemListElement":[{"@type":"ListItem","position":1,"name":"\u9996\u9875","item":"https:\/\/www.pyrazoles-derivatives.com\/"},{"@type":"ListItem","position":2,"name":"Makisumi, Yasuo’s team published research in Chemical & Pharmaceutical Bulletin in 10 | CAS: 3553-12-6"}]},{"@type":"WebSite","@id":"https:\/\/www.pyrazoles-derivatives.com\/#website","url":"https:\/\/www.pyrazoles-derivatives.com\/","name":"pyrazoles-derivatives","description":"Several pyrazole derivatives possess important pharmacological activities and they have been proved useful materials in drug research. Pyrazole derivatives play an important role in antitumor agents.","potentialAction":[{"@type":"SearchAction","target":{"@type":"EntryPoint","urlTemplate":"https:\/\/www.pyrazoles-derivatives.com\/?s={search_term_string}"},"query-input":{"@type":"PropertyValueSpecification","valueRequired":true,"valueName":"search_term_string"}}],"inLanguage":"en-US"},{"@type":"Person","@id":"https:\/\/www.pyrazoles-derivatives.com\/#\/schema\/person\/d9a9f27bed675392c6f363a01ffd49f1","name":"Jessica.F","image":{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/www.pyrazoles-derivatives.com\/#\/schema\/person\/image\/","url":"https:\/\/en.cravatar.com\/avatar\/2d1cec2a99eeaad5a5b217c9cdbfb610?s=96&d=mm&r=g","contentUrl":"https:\/\/en.cravatar.com\/avatar\/2d1cec2a99eeaad5a5b217c9cdbfb610?s=96&d=mm&r=g","caption":"Jessica.F"}}]}},"_links":{"self":[{"href":"https:\/\/www.pyrazoles-derivatives.com\/index.php?rest_route=\/wp\/v2\/posts\/11779","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.pyrazoles-derivatives.com\/index.php?rest_route=\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.pyrazoles-derivatives.com\/index.php?rest_route=\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.pyrazoles-derivatives.com\/index.php?rest_route=\/wp\/v2\/users\/8"}],"replies":[{"embeddable":true,"href":"https:\/\/www.pyrazoles-derivatives.com\/index.php?rest_route=%2Fwp%2Fv2%2Fcomments&post=11779"}],"version-history":[{"count":0,"href":"https:\/\/www.pyrazoles-derivatives.com\/index.php?rest_route=\/wp\/v2\/posts\/11779\/revisions"}],"wp:attachment":[{"href":"https:\/\/www.pyrazoles-derivatives.com\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=11779"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.pyrazoles-derivatives.com\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=11779"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.pyrazoles-derivatives.com\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=11779"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}