Selective cyclisation of 2, 3, 4, 5-tetra-O-acetyl-galactaric acid bis-[Alkylthio(thiocarbonyl)]hydrazide to Saccharide 1, 3, 4-Oxadiazole, Thiadiazole, and thiadiazoline derivatives
The synthesis of galactaric acid acetate bis[alkylthio(thiocarbonyl)]hydrazide (1, 2) is described. Selective cyclisation of both hydrazides 1 and 2 was investigated. Phosphorous oxychloride as cyclising agent led to dehydrative cyclisation and produced 1, 2, 3, 4‐tetra‐O‐acetyl‐1, 4‐bis(5‐S‐methyl...
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| Veröffentlicht in: | Journal für Praktische Chemie 1991, Vol.333 (2), p.339-344 |
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| container_title | Journal für Praktische Chemie |
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| creator | Mansour, El-Sayed M. E. Kassem, Ahmed A. Abass, Tarek M. El-Toukhy, Ahmed A. Nassr, M. A. |
| description | The synthesis of galactaric acid acetate bis[alkylthio(thiocarbonyl)]hydrazide (1, 2) is described. Selective cyclisation of both hydrazides 1 and 2 was investigated. Phosphorous oxychloride as cyclising agent led to dehydrative cyclisation and produced 1, 2, 3, 4‐tetra‐O‐acetyl‐1, 4‐bis(5‐S‐methyl or — benzyl) 1, 3, 4‐thiadiazol‐2‐yl galactotetritol (3) or (4). While thionyl chloride led to dehydrosulfurization and gave 1, 2, 3, 4‐tetra‐O‐acetyl‐1, 4‐bis(5‐S‐methyl or ‐benzyl)‐1, 3, 4‐oxadiazol‐2‐yl galactotetritol (5) or (6). Finally with triethyl orthoformate as cyclising agent, compounds 1 or 2, gave 3, 3′‐(2, 3, 4, 5‐tetra‐O‐acetyl‐galactar‐1.6 dioyl)bis[2‐ethoxy‐2, 3‐dihydro‐5‐S‐methyl or benzyl 1, 3, 4‐thiadiazole] (7) or (8). |
| doi_str_mv | 10.1002/prac.19913330221 |
| format | Article |
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Finally with triethyl orthoformate as cyclising agent, compounds 1 or 2, gave 3, 3′‐(2, 3, 4, 5‐tetra‐O‐acetyl‐galactar‐1.6 dioyl)bis[2‐ethoxy‐2, 3‐dihydro‐5‐S‐methyl or benzyl 1, 3, 4‐thiadiazole] (7) or (8).</description><identifier>ISSN: 0021-8383</identifier><identifier>EISSN: 1521-3897</identifier><identifier>DOI: 10.1002/prac.19913330221</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag GmbH</publisher><ispartof>Journal für Praktische Chemie, 1991, Vol.333 (2), p.339-344</ispartof><rights>Copyright © 1991 Verlag GmbH & Co. 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While thionyl chloride led to dehydrosulfurization and gave 1, 2, 3, 4‐tetra‐O‐acetyl‐1, 4‐bis(5‐S‐methyl or ‐benzyl)‐1, 3, 4‐oxadiazol‐2‐yl galactotetritol (5) or (6). Finally with triethyl orthoformate as cyclising agent, compounds 1 or 2, gave 3, 3′‐(2, 3, 4, 5‐tetra‐O‐acetyl‐galactar‐1.6 dioyl)bis[2‐ethoxy‐2, 3‐dihydro‐5‐S‐methyl or benzyl 1, 3, 4‐thiadiazole] (7) or (8).</description><issn>0021-8383</issn><issn>1521-3897</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1991</creationdate><recordtype>article</recordtype><recordid>eNqFkE1PHDEMhiNUpG6h9x5zpNKGJpPJfBx62K5a2oJYCishtUKRx8mwKekOSiLK8MP4fcxoEdBTfbBly89r6yXkneD7gvPsw3UA3Bd1LaSUPMvEFpkIlQkmq7p8RSbDimCVrORr8ibG35xzWeTlhNyfWW8xuRtLsUfvIiTXrWnX0mxK5ZTmU6pYsikAWzBAm3rPLsEDJggOKaAztHGR_Zr5q96nlev2xoQQmm7d-_cXq94EuHPG0tTRM0BcDeDQiY08W9yCcXDXeTuly5V7bmBtaHoauLWlxgZ3A-OvcZdst-CjfftYd8jyy-fl_Cs7Whx8m8-OGIqKC5a1w0ErTVUJNQY3hZLKQJPnquWFEkVujcGmVgqxhryWlW1atHVbIkgjdwjfyGLoYgy21dfB_YHQa8H1aLsebdcvbB-Qjxvkr_O2_---Pjmdzf_l2YZ3MdnbJx7ClS5KWSp9fnygD0-z7z_kyU_9ST4A8vKZ2A</recordid><startdate>1991</startdate><enddate>1991</enddate><creator>Mansour, El-Sayed M. 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E.</creatorcontrib><creatorcontrib>Kassem, Ahmed A.</creatorcontrib><creatorcontrib>Abass, Tarek M.</creatorcontrib><creatorcontrib>El-Toukhy, Ahmed A.</creatorcontrib><creatorcontrib>Nassr, M. A.</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>Journal für Praktische Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mansour, El-Sayed M. E.</au><au>Kassem, Ahmed A.</au><au>Abass, Tarek M.</au><au>El-Toukhy, Ahmed A.</au><au>Nassr, M. A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Selective cyclisation of 2, 3, 4, 5-tetra-O-acetyl-galactaric acid bis-[Alkylthio(thiocarbonyl)]hydrazide to Saccharide 1, 3, 4-Oxadiazole, Thiadiazole, and thiadiazoline derivatives</atitle><jtitle>Journal für Praktische Chemie</jtitle><addtitle>J. Prakt. Chem</addtitle><date>1991</date><risdate>1991</risdate><volume>333</volume><issue>2</issue><spage>339</spage><epage>344</epage><pages>339-344</pages><issn>0021-8383</issn><eissn>1521-3897</eissn><abstract>The synthesis of galactaric acid acetate bis[alkylthio(thiocarbonyl)]hydrazide (1, 2) is described. Selective cyclisation of both hydrazides 1 and 2 was investigated. Phosphorous oxychloride as cyclising agent led to dehydrative cyclisation and produced 1, 2, 3, 4‐tetra‐O‐acetyl‐1, 4‐bis(5‐S‐methyl or — benzyl) 1, 3, 4‐thiadiazol‐2‐yl galactotetritol (3) or (4). While thionyl chloride led to dehydrosulfurization and gave 1, 2, 3, 4‐tetra‐O‐acetyl‐1, 4‐bis(5‐S‐methyl or ‐benzyl)‐1, 3, 4‐oxadiazol‐2‐yl galactotetritol (5) or (6). Finally with triethyl orthoformate as cyclising agent, compounds 1 or 2, gave 3, 3′‐(2, 3, 4, 5‐tetra‐O‐acetyl‐galactar‐1.6 dioyl)bis[2‐ethoxy‐2, 3‐dihydro‐5‐S‐methyl or benzyl 1, 3, 4‐thiadiazole] (7) or (8).</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag GmbH</pub><doi>10.1002/prac.19913330221</doi><tpages>6</tpages></addata></record> |
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| ispartof | Journal für Praktische Chemie, 1991, Vol.333 (2), p.339-344 |
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| language | eng |
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| source | Wiley Online Library - AutoHoldings Journals |
| title | Selective cyclisation of 2, 3, 4, 5-tetra-O-acetyl-galactaric acid bis-[Alkylthio(thiocarbonyl)]hydrazide to Saccharide 1, 3, 4-Oxadiazole, Thiadiazole, and thiadiazoline derivatives |
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