Metal free direct formation of various substituted pyrido[2 ',1 ': 2,3]imidazo[4,5-c]isoquinolin-5-amines and their further functionalization

Tber Z.; Hiebel M. -A.; Allouchi H.; El Hakmaoui A.; Akssira M.; Guillaumet G.; Berteina-Raboin S.

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Metal free direct formation of various substituted pyrido[2 ',1 ': 2,3]imidazo[4,5-c]isoquinolin-5-amines and their further functionalization

机译：无金属直接形成各种取代的吡啶[2'，1'：2,3]咪唑唑[4,5-C]异喹啉-5-胺及其进一步的官能化

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Original substituted pyrido[2',1':2,3] imidazo[4,5-c] isoquinolin-5-amines have been prepared following a Groebke-Blackburn-Bienayme MCR combined with an N-deprotection and a spontaneous final cyclization step in moderate to good yields. The flexibility of the described method enables the introduction of diverse groups in the 6 and 7 positions on the resulting scaffold using commercially available starting materials. Furthermore, a Buchwald-Hartwig cross coupling with a wide range of aryl and hetaryl halides has been successfully reported using our heterocyclic primary amine derivatives.

机译：在Groebke-Blackburn-Bienayme MCR结合N-脱保护和自发的最终环化步骤后制备了原始取代的吡啶[2'，1'：2,3]咪唑啉[4,5-C]异喹啉-5-胺在中度到良好的收益率。所描述的方法的灵活性使得能够使用市售的起始材料在所得到的支架上引入6和7位的不同组。此外，使用杂环伯胺衍生物成功地报道了具有宽范围芳基和Hetaryl卤化物的Buchwald-Hartwig交叉耦合。

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《RSC Advances》 |2015年第44期|共10页
作者
Tber Z.; Hiebel M. -A.; Allouchi H.; El Hakmaoui A.; Akssira M.; Guillaumet G.; Berteina-Raboin S.;
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作者单位

Univ Orleans Inst Chim Organ &

Analyt UMR CNRS 7311 F-45067 Orleans France;

Univ Orleans Inst Chim Organ &

Analyt UMR CNRS 7311 F-45067 Orleans France;

Univ Tours Lab Phys Equipe RICM UMR ISP 1282 Tours France;

URAC 22 Univ Hassan II Mohammedia Casablanca Equipe Chim Bioorgan &

Analyt Mohammadia 28800 Morocco;

URAC 22 Univ Hassan II Mohammedia Casablanca Equipe Chim Bioorgan &

Analyt Mohammadia 28800 Morocco;

Univ Orleans Inst Chim Organ &

Analyt UMR CNRS 7311 F-45067 Orleans France;

Univ Orleans Inst Chim Organ &

Analyt UMR CNRS 7311 F-45067 Orleans France;

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正文语种 eng
中图分类化学;
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1. Metal free direct formation of various substituted pyrido[2 ',1 ': 2,3]imidazo[4,5-c]isoquinolin-5-amines and their further functionalization [J] . Tber Z., Hiebel M. -A., Allouchi H., RSC Advances . 2015,第44期

机译：无金属直接形成各种取代的吡啶[2'，1'：2,3]咪唑唑[4,5-C]异喹啉-5-胺及其进一步的官能化
2. Metal-free C-N bond formations: one-pot synthesis of pyrido[2 ',1 ':2,3]imidazo[4,5-c]cinnolines, benzo[4 ',5 ']thiazolo- and thiazolo [2 ',3 ':2,3]imidazo[4,5-c]cinnolines (vol 6, pg 67086, 2016) [J] . Kandimalla Satheeshkumar Reddy, Sabitha Gowravaram RSC Advances . 2016,第75期

机译：无金属Cn键组：1罐Pyrido合成[2'，1'：2,3]咪唑唑[4,5-C]肉碱，苯并[4'，5']噻唑-和噻唑醇[2'， 3'：2,3]伊米达佐[4,5-C]肉碱（Vol 6，PG 67086,2016）
3. Correction: Metal-free C–N bond formations: one-pot synthesis of pyrido[2′,1′:2,3]imidazo[4,5-c]cinnolines, benzo[4′,5′]thiazolo- and thiazolo[2′,3′:2,3]imidazo[4,5-c]cinnolines [J] . Satheeshkumar Reddy Kandimalla, Gowravaram Sabitha RSC Advances . 2016,第75期

机译：校正：无金属C-N键形成：吡啶的单罐合成[2'，1'：2,3]咪咪扎索[4,5-C]肉碱，苯并[4'，5']噻唑-和噻唑[2'，3'：2,3]咪咪卓[4,5-c]辣椒碱
4. Efficient synthesis of 3H-imidazo4',5':5,6pyrido2,3-dpyrimidin-8-amine 7-oxide in mild conditions [C] . A. Ribeiro, A. M. Carvalho, M. F. Proenca European Symposium on Organic Chemistry . 2009

机译：高效合成3H-咪唑4'，5'：5,6 Pyrido 2,3-D嘧啶-8-胺7-氧化物在温和条件下
5. Synthesis of benzo[a]carbazoles and indolo[2,3-a]carbazoles using a combined directed ortho metalation-cross coupling strategy. [D] . Cai, Xiongwei. 2006

机译：苯并[a]咔唑和吲哚[2,3-a]咔唑的合成使用定向定向金属交叉偶联策略。
6. 1-Phenyl-6,7,8,9-hexahydro-1H,5H-cyclohepta[1′,2′:2,3]pyrido[6,5-c]pyrazol-4-amine: a new tacrine analogue [O] . Lijun Zhang, Daxin Shi, Jiarong Li, 2015

机译：1-苯基-6,7,8,9-六氢-1H，5H-环庚七[1'，2'：2,3]吡啶[6,5-c]吡唑-4-胺：一种新的他克林类似物
7. 6-Benzyl-3,4-dimethoxy-10-methylpyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-one [O] . Meindl, Kathrin, Stern, Daniel, Mert-Balci, Fadime, 2009

机译：6-苄基-3,4-二甲基氧基-10-甲基吡啶[2'，1'：2,3]咪唑并[4,5-c]异喹啉-5（6H）-
8. Organotransition-Metal Metallacarboranes. 9. Nido-2,3-Dibenzyl-2,3-dicarbahexaborane(8) ((PhCH2)2C2B4H6), a Versatile Multifunctional nido-Carborane: Iron-Polyarene Sandwich Compounds and Chromium Tricarbonyl pi-Complexes [R] . Spencer, J. T., Grimes, R. N. 1987

机译：有机过渡 - 金属金属碳硼烷。 9.Nido-2,3-二苄基-2,3-二碳六硼烷（8）（（phCH2）2C2B4H6），多功能多官能nido-碳硼烷：铁 - 聚芳烃夹心化合物和三羰基铬π配合物

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Metal free direct formation of various substituted pyrido[2 ',1 ': 2,3]imidazo[4,5-c]isoquinolin-5-amines and their further functionalization

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