A novel and one pot synthesis of ethyl 7,12-dihydro-1,3,6,7,12-pentaazapleiadene-5-carboxylates

Basetti Vishnu; Poturaju Venkatanarayana; Hosahalli Subramanya; Potluri Vijay

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A novel and one pot synthesis of ethyl 7,12-dihydro-1,3,6,7,12-pentaazapleiadene-5-carboxylates

机译：一种新颖的一锅合成7,12-二氢-1,3,6,7,12-五氮杂紫丁烯-5-羧酸乙酯

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A new tandem three-step synthesis of ethyl 7,12-dihydro-1,3,6,7,12-pentaazapleiadene-5-carboxylate derivatives (9a-j) has been accomplished stepwise. Reaction of 4-chloro-6-methylpyrimidine-5-carbonitrile with various 4-substituted 2-nitrohenzeneamines yielded the corresponding 4-(2-nitrophenylamino)-6-methylpyrimidine-5-carbonitriles (7a-j). These phenylamino methylpyrimidines reacted with diethyl oxalate to furnish (Z)-ethyl 3-(6-(2-nitrophenylamino)-5cyanopyrimidin-4-yl)-2-hydroxyacrylates (8a-j). The resulting (Z)-ethyl 3-(6-(2-nitrophenylamino)-5-cyanopyrimidin-4-yl)-2-hydroxyacrylates on reduction with SnCl2 center dot 2H(2)O in ethanol underwent cyclization to afford the desired products in good to very good yields.

机译：7,12-dihydro-1,3,6,7,12-pentaazapleiadene-5-羧酸盐衍生物（9a-j）的新的串联三步合成法已经完成。 4-氯-6-甲基嘧啶-5-腈与各种4-取代的2-硝基苯胺反应，得到相应的4-（2-硝基苯基氨基）-6-甲基嘧啶-5-腈（7a-j）。这些苯基氨基甲基嘧啶与草酸二乙酯反应，得到3-（6-（2-（2-硝基苯基氨基）-5氰基嘧啶-4-基）-2-羟基丙烯酸（Z）-乙基酯（8a-j）。在乙醇中用SnCl2中心点2H（2）O还原后生成的（Z）-乙基3-（6-（2-硝基苯基氨基）-5-氰基嘧啶丁-4-基）-2-羟基丙烯酸酯进行环化反应，得到所需产物产量很高。

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来源
《Journal of the Indian Chemical Society》 |2015年第6期|共4页
作者
Basetti Vishnu; Poturaju Venkatanarayana; Hosahalli Subramanya; Potluri Vijay;
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正文语种 eng
中图分类化学;
关键词
4-Chloro-6-methylpyrimidine-5-carbonitrile; pentaazapleiadenes; stannous chloride; domino method;

机译：4-氯-6-甲基嘧啶-5-腈;五氮杂庚烯;氯化锡;多米诺法;

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1. A novel and one pot synthesis of ethyl 7,12-dihydro-1,3,6,7,12-pentaazapleiadene-5-carboxylates [J] . Basetti Vishnu, Poturaju Venkatanarayana, Hosahalli Subramanya, Journal of the Indian Chemical Society . 2015,第6期

机译：一种新颖的一锅合成7,12-二氢-1,3,6,7,12-五氮杂紫丁烯-5-羧酸乙酯
2. Selective hydrolysis of ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylate and ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylate as a key step in the large-scale synthesis of bicyclic heteroaryl carboxyaldehydes [J] . Nikitenko AA, Winkley MW, Zeldis J, Organic process research & development . 2006,第4期

机译：5,6-二氢-4H-吡咯并[1,2-b]吡唑-2-羧酸乙酯和5,6-二氢-4H-吡咯并[1,2-b]吡唑-3-羧酸乙酯的选择性水解大规模合成双环杂芳基羧醛的关键步骤
3. One-pot, multi-component synthesis of ethyl (E)-1-(3-ethoxy-3-oxoprop-1-en-1-yl)-2-aryl-2,5-dihydro-1H-benzo[b][1,4]diazepine-3-carboxylate derivatives [J] . Tan Hong-bo, Wang Yin-feng, Xu Jia, Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2020,第11期

机译：单壶，多组分合成乙基（e）-1-（3-乙氧基-3-氧化丙丙-1-烯-1-基）-2-芳基-2,5-二氢-1H-苯并[B] [1,4]二氮杂-3-羧酸酯衍生物
4. Catalytic performance of CuO@SiO2 for one-pot synthesis of pyrimidine derivative,ethyl 6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate [C] . A H Cahyana, S P Sari, B Ardiansah International Symposium on Current Progress in Functional Materials . 2019

机译：CuO / 2-oxo-4-苯基-1,2,3,4-四氢嘧啶-5-羧酸乙烯基二罐合成CuO / 2-氧代-4-苯基-1,2,3,4-四氢嘧啶-5-羧酸酯的催化性能
5. Part I. One-pot synthesis of secondary alcohols and one-pot asymmetric synthesis of secondary propargylic alcohols. Part II. Redox isomerization of secondary propargylic alcohols to enones. Part III. Synthesis study towards C9-C14 fragment of (+)-discodermolide. Part IV. Asymmetric synthesis of anti, anti-stereotriad building blocks for polypropionate natural products [D] . Xie, Qiuzhe 2007

机译：第一部分：仲醇的一锅法合成和仲炔丙醇的一锅法不对称合成。第二部分仲炔丙醇的氧化还原异构化为烯酮。第三部分（+）-discodermolide C9-C14片段的合成研究。第四部分聚丙烯酸酯天然产物的抗，抗立体三环构建基的不对称合成
6. Multiple-Step One-Pot Synthesis of 2-Substituted-3-phosphono-1-thia-4-aza-2-Cyclohexene-5-Carboxylates and Their Corresponding Ethyl Esters [O] . Dunxin Shen, Kenneth Hensley, Travis T. Denton -1

机译：2-取代的-3-膦酰基-1-硫杂-4-氮杂-2-环己烯-5-羧酸酯及其相应的乙基酯的多步一锅合成
7. 1,6-Dihydro-3(2H)-pyridinones. IV. Synthesis of (.+-.)-tabersonine and (.+-.)-cleavamine via a common intermediate, ethyl 3-ethyl-3-hydroxy-1,2,3,6-tetrahydropyridine-1-carboxylate. [O] . TAKESHI IMANISHI, HIROAKI SHIN, NORIYUKI YAGI, 1983

机译：1,6-二氢-3（2H） - 吡啶酮。 IV。（。+ - 。） - Tabersonine和（。+ - 。） - 通过常见中间体，乙基3-乙基-3-羟基-1,2,3,6-四氢吡啶-1-羧酸酯的Cleavamine。

A novel and one pot synthesis of ethyl 7,12-dihydro-1,3,6,7,12-pentaazapleiadene-5-carboxylates

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