Solvent-Controlled, Site-Selective N-Alkylation Reactions of Azolo-Fused Ring Heterocycles at N1-, N2-, and N3-Positions, Including Pyrazolo[3,4-d]pyrimidines, Purines, [1,2,3]Triazolo[4,5]pyridines, and Related Deaza-Compounds

Brett C. Bookser; Michael I. Weinhouse; Aaron C. Burns; Andrew N. Valiere; Lino J. Valdez; Pawel Stanczak; Jim Na; Arnold L. Rheingold; Curtis E. Moore; Brian Dyck

首页> 外文期刊>The Journal of Organic Chemistry >Solvent-Controlled, Site-Selective N-Alkylation Reactions of Azolo-Fused Ring Heterocycles at N1-, N2-, and N3-Positions, Including Pyrazolo[3,4-d]pyrimidines, Purines, [1,2,3]Triazolo[4,5]pyridines, and Related Deaza-Compounds

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Solvent-Controlled, Site-Selective N-Alkylation Reactions of Azolo-Fused Ring Heterocycles at N1-, N2-, and N3-Positions, Including Pyrazolo[3,4-d]pyrimidines, Purines, [1,2,3]Triazolo[4,5]pyridines, and Related Deaza-Compounds

机译：溶剂控制的，位点 - 选择性氮杂稠环环杂环在N1-，N 2和N 3 - 位置，包括吡唑[3,4- D ]嘧啶，嘌呤，[1,2,3]三亚唑[4,5]吡啶，以及相关的Deaza-化合物

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机译：<！[CDATA [4-甲氧基-1的烷基化-1]，使用NaHMDS选择性地提供N2-甲基产品4，在THF中用碘甲烷的碘甲烷嘧啶（ 1b）嘧啶（ 1b） - 在N1-甲基产物（ 2b）上的8/1比例下，甲氧基-2-甲基-2嘧啶（ 3b）以8/1的比例为8/1的比例。有趣的是，在DMSO反转的选择性中进行反应，以提供4/1的N1 / N 2甲基化产物的比例。用N1和N7的产品晶体结构与钠配位，表明后者加强N2选择性的潜在作用。用26个杂拷物测试选择性极限，所述杂拷迹显示N7是指示烷基化的控制元件，以便在THF中进行吡唑和三唑稠环杂环的吡唑-和N 3的N 2。使用〜（1）H检测脉冲场梯度刺激的回波（PFG-STE）NMR限定了离子反应复合物的分子量。该数据和DFT电荷分布计算表明THF和溶剂分离的离子对（啜饮）中的封闭离子对（CIP）或紧密离子对（尖端）是DMSO中的反应性物种。]>

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《The Journal of Organic Chemistry》 |2018年第12期|共20页
作者
Brett C. Bookser; Michael I. Weinhouse; Aaron C. Burns; Andrew N. Valiere; Lino J. Valdez; Pawel Stanczak; Jim Na; Arnold L. Rheingold; Curtis E. Moore; Brian Dyck;
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Departments of Medicinal Chemistry Structural Biology and Scientific Computing;

Departments of Medicinal Chemistry Structural Biology and Scientific Computing;

Departments of Medicinal Chemistry Structural Biology and Scientific Computing;

Departments of Medicinal Chemistry Structural Biology and Scientific Computing;

Departments of Medicinal Chemistry Structural Biology and Scientific Computing;

Departments of Medicinal Chemistry Structural Biology and Scientific Computing;

Departments of Medicinal Chemistry Structural Biology and Scientific Computing;

Department of Chemistry Crystallography Laboratory University of California;

Department of Chemistry Crystallography Laboratory University of California;

Departments of Medicinal Chemistry Structural Biology and Scientific Computing;

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1. Solvent-Controlled, Site-Selective N-Alkylation Reactions of Azolo-Fused Ring Heterocycles at N1-, N2-, and N3-Positions, Including Pyrazolo[3,4-d]pyrimidines, Purines, [1,2,3]Triazolo[4,5]pyridines, and Related Deaza-Compounds [J] . Brett C. Bookser, Michael I. Weinhouse, Aaron C. Burns, The Journal of Organic Chemistry . 2018,第12期

机译：溶剂控制的，位点 - 选择性氮杂稠环环杂环在N1-，N 2和N 3 - 位置，包括吡唑[3,4- D ]嘧啶，嘌呤，[1,2,3]三亚唑[4,5]吡啶，以及相关的Deaza-化合物
2. UTILITY OF CYANOACETAMIDES AS PRECURSORS TO PYRAZOLO-[3,4-d]PYRIMIDIN-4-ONES,2-ARYL-6-SUBSTITUTED 1,2,3-TRIAZOLO-[4,5-d]jPYRIMIDINES AND PYRAZOLO[l,5-a]PYRIMIDINE-3-CARBOXAMIDES [J] . Hamada Mohamed Ibrahim, Saad Makhseed, Ramadan Maawad Abdel-MotaIeb Heterocycles: An International Journal for Reviews and Communications in Heterocyclic Chemistry . 2007,第9期

机译：氰基酰胺作为吡咯并[[3,4-d]嘧啶-4-酮，2-ARYL-6取代的1,2,3-三唑并[[4,5-d]]嘧啶和吡唑并[1,5]前体的用途-a]嘧啶-3-羧酰胺
3. Pyrazolo[3,4-d][1,2,3]triazolo[1,5-a]pyrimidine:a new ring system through Dimroth rearrangement [J] . Antonino Lauria, Ilenia Abbate, Chiara Patella Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2008,第35期

机译：吡唑并[3,4-d] [1,2,3]三唑并[1,5-a]嘧啶：通过Dimroth重排的新环系统

Solvent-Controlled, Site-Selective N-Alkylation Reactions of Azolo-Fused Ring Heterocycles at N1-, N2-, and N3-Positions, Including Pyrazolo[3,4-d]pyrimidines, Purines, [1,2,3]Triazolo[4,5]pyridines, and Related Deaza-Compounds

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