D. Boger, J. Panek, Mona Patel
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{"title":"反应性缺电子杂环偶氮二烯:二甲基1,2,4,5‐四嗪‐3,6‐二羧酸盐的制备和Diels‐Alder反应。1,2‐二嗪(二甲基4‐苯基‐1,2‐二嗪‐3,6‐二羧酸盐)和吡咯(二甲基3‐苯基吡咯‐2,5‐二羧酸盐)介绍","authors":"D. Boger, J. Panek, Mona Patel","doi":"10.1002/0471264180.OS070.10","DOIUrl":null,"url":null,"abstract":"Preparation and Diels-Alder reaction of a reactive, electron-deficient heterocyclic azadiene: dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate. 1,2-diazine (dimethyl 4-phenyl-1,2-diazine-3,6-dicarboxylate) and pyrrole (dimethyl 3-phenylpyrrole-2,5-dicarboxylate) introduction \n \n \n \nintermediate: Disodium dihydro-1,2,4,5-tetrazine-3,6-dicarboxylate \n \n \n \n \nintermediate: Dihydro-1,2,4,5-tetrazine-3,6-dicarboxylic acid \n \n \n \n \nintermediate: Dimethyl dihydro-1,2,4,5-tetrazine-3,6-dicarboxylate \n \n \n \n \nproduct: Dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate \n \n \n \n \nproduct: Dimethyl 4-phenyl-1,2-diazine-3,6-dicarboxylate \n \n \n \n \nproduct: Dimethyl 3-phenylpyrrole-2,5-dicarboxylate \n \n \n \n \nbyproduct: methyl 3-phenyl-5-carboxamidopyrrole-2-carboxylate \n \n \n \n \n \nKeywords: \n \nannulation, heterocyclic-[5]; \nannulation, heterocyclic-[6]; \nannulation, heterocyclic-[6]; \ncyclization, cycloaddition; \nDiels-Alder reactions; \nesterification, of dicarboxylic acids; \noxidation, miscellaneous; \nreduction, miscellaneous; \nring contraction reactions; \nmethanol; \nnitrous gases, generation; \nzinc dust, activation; \ndiazo compounds; \ndioxane, cancer suspect agent; \nnitrous gases, toxic; \nnitrous gases, toxic","PeriodicalId":19576,"journal":{"name":"Organic Syntheses","volume":null,"pages":null},"PeriodicalIF":0.7000,"publicationDate":"2003-04-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"5","resultStr":"{\"title\":\"Preparation and Diels‐Alder Reaction of a Reactive, Electron‐Deficient Heterocyclic Azadiene: Dimethyl 1,2,4,5‐Tetrazine‐3,6‐Dicarboxylate. 1,2‐Diazine (Dimethyl 4‐Phenyl‐1,2‐Diazine‐3,6‐Dicarboxylate) and Pyrrole (Dimethyl 3‐Phenylpyrrole‐2,5‐Dicarboxylate) Introduction\",\"authors\":\"D. Boger, J. Panek, Mona Patel\",\"doi\":\"10.1002/0471264180.OS070.10\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Preparation and Diels-Alder reaction of a reactive, electron-deficient heterocyclic azadiene: dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate. 1,2-diazine (dimethyl 4-phenyl-1,2-diazine-3,6-dicarboxylate) and pyrrole (dimethyl 3-phenylpyrrole-2,5-dicarboxylate) introduction \\n \\n \\n \\nintermediate: Disodium dihydro-1,2,4,5-tetrazine-3,6-dicarboxylate \\n \\n \\n \\n \\nintermediate: Dihydro-1,2,4,5-tetrazine-3,6-dicarboxylic acid \\n \\n \\n \\n \\nintermediate: Dimethyl dihydro-1,2,4,5-tetrazine-3,6-dicarboxylate \\n \\n \\n \\n \\nproduct: Dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate \\n \\n \\n \\n \\nproduct: Dimethyl 4-phenyl-1,2-diazine-3,6-dicarboxylate \\n \\n \\n \\n \\nproduct: Dimethyl 3-phenylpyrrole-2,5-dicarboxylate \\n \\n \\n \\n \\nbyproduct: methyl 3-phenyl-5-carboxamidopyrrole-2-carboxylate \\n \\n \\n \\n \\n \\nKeywords: \\n \\nannulation, heterocyclic-[5]; \\nannulation, heterocyclic-[6]; \\nannulation, heterocyclic-[6]; \\ncyclization, cycloaddition; \\nDiels-Alder reactions; \\nesterification, of dicarboxylic acids; \\noxidation, miscellaneous; \\nreduction, miscellaneous; \\nring contraction reactions; \\nmethanol; \\nnitrous gases, generation; \\nzinc dust, activation; \\ndiazo compounds; \\ndioxane, cancer suspect agent; \\nnitrous gases, toxic; \\nnitrous gases, toxic\",\"PeriodicalId\":19576,\"journal\":{\"name\":\"Organic Syntheses\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":0.7000,\"publicationDate\":\"2003-04-28\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"5\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Syntheses\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1002/0471264180.OS070.10\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Syntheses","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1002/0471264180.OS070.10","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 5
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摘要
反应性缺电子杂环偶氮二甲基1,2,4,5-四嗪-3,6-二羧酸酯的制备及diols - alder反应。1,2-二嗪(二甲基4-苯基-1,2-二嗪-3,6-二羧酸盐)和吡咯(二甲基3-苯基吡咯-2,5-二羧酸盐)引入中间体:二氢二钠-1,2,4,5-四嗪-3,6-二羧酸盐中间体:二氢二氢-1,2,4,5-四嗪-3,6-二羧酸盐中间体:二甲基二氢-1,2,4,5-四嗪-3,6-二羧酸盐产品:二甲基1,2,4,5-四嗪-3,6-二羧酸盐产品:二甲基4-苯基-1,2-二嗪-3,6-二羧酸盐产品:二甲基3-苯基吡咯-2,5-二羧酸酯副产物:甲基3-苯基-5-羧氨基吡咯-2-羧酸酯关键词:环状;杂环;环状结构,杂环- [6];环状结构,杂环- [6];环化,环加成作用;Diels-Alder反应;二羧酸的酯化反应;氧化,各种各样的;减少,各种各样的;环收缩反应;甲醇;产生亚氮气体;锌粉,活化;重氮的化合物;二恶烷,癌症怀疑剂;含氮气体,有毒;氮气,有毒
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Preparation and Diels‐Alder Reaction of a Reactive, Electron‐Deficient Heterocyclic Azadiene: Dimethyl 1,2,4,5‐Tetrazine‐3,6‐Dicarboxylate. 1,2‐Diazine (Dimethyl 4‐Phenyl‐1,2‐Diazine‐3,6‐Dicarboxylate) and Pyrrole (Dimethyl 3‐Phenylpyrrole‐2,5‐Dicarboxylate) Introduction
Preparation and Diels-Alder reaction of a reactive, electron-deficient heterocyclic azadiene: dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate. 1,2-diazine (dimethyl 4-phenyl-1,2-diazine-3,6-dicarboxylate) and pyrrole (dimethyl 3-phenylpyrrole-2,5-dicarboxylate) introduction
intermediate: Disodium dihydro-1,2,4,5-tetrazine-3,6-dicarboxylate
intermediate: Dihydro-1,2,4,5-tetrazine-3,6-dicarboxylic acid
intermediate: Dimethyl dihydro-1,2,4,5-tetrazine-3,6-dicarboxylate
product: Dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate
product: Dimethyl 4-phenyl-1,2-diazine-3,6-dicarboxylate
product: Dimethyl 3-phenylpyrrole-2,5-dicarboxylate
byproduct: methyl 3-phenyl-5-carboxamidopyrrole-2-carboxylate
Keywords:
annulation, heterocyclic-[5];
annulation, heterocyclic-[6];
annulation, heterocyclic-[6];
cyclization, cycloaddition;
Diels-Alder reactions;
esterification, of dicarboxylic acids;
oxidation, miscellaneous;
reduction, miscellaneous;
ring contraction reactions;
methanol;
nitrous gases, generation;
zinc dust, activation;
diazo compounds;
dioxane, cancer suspect agent;
nitrous gases, toxic;
nitrous gases, toxic