Efficient Solid-Phase Synthesis of Highly Functionalized 1,4-Benzodiazepin-5-one Derivatives and Related Compounds by Intramolecular Aza-Wittig Reactions

Carmen Gil; Stefan Brase

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Efficient Solid-Phase Synthesis of Highly Functionalized 1,4-Benzodiazepin-5-one Derivatives and Related Compounds by Intramolecular Aza-Wittig Reactions

机译：分子内的Aza-Wittig反应高效固相合成高官能度的1,4-苯并二氮杂-5-酮衍生物和相关化合物

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Due to their widespread biological activities and favorable pharma-cokinetic properties,benzodiazepines were among the first classes of small molecules to be synthesized on solid supports.Since then,there have been numerous reports on the synthesis of similar skeletons.We have employed the Tl triazene linker to yield 1,4-ben-zodiazepin-5-one.Starting from various substituted triazene resins,cleavage in the presence of an azide donor,such as trimethylsilylazide,gave rise to aryl azides.Intramolecular aza-Wittig reactions produced the appropriately func-tionalized N-heterocycles.By using this route,the natural product deoxyvasici-none and related compounds were prepared.

机译：由于苯二氮卓类药物具有广泛的生物活性和良好的药代动力学特性，因此它们是在固体载体上合成的第一类小分子。从那时起，已有许多关于合成类似骨架的报道。我们使用了Tl三氮烯从各种取代的三嗪树脂开始，在叠氮化物供体（如三甲基甲硅烷基叠氮化物）的存在下裂解，生成芳基叠氮化物。分子内的氮杂-Wittig反应产生适当的功能归一化的N-杂环。通过这种途径，制备了天然产物脱氧vasicinone和相关化合物。

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《Chemistry: A European journal》 |2005年第9期|共9页
作者
Carmen Gil; Stefan Brase;
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正文语种 eng
中图分类化学;
关键词
aza-Wittig reaction; benzodiazepines; heterocycles; solid-phase synthesis; traceless linker;

机译：氮杂-维蒂希反应;苯并二氮杂;杂环;固相合成;无痕连接体;

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1. Efficient Solid-Phase Synthesis of Highly Functionalized 1,4-Benzodiazepin-5-one Derivatives and Related Compounds by Intramolecular Aza-Wittig Reactions [J] . Carmen Gil, Stefan Brase Chemistry: A European journal . 2005,第9期

机译：分子内的Aza-Wittig反应高效固相合成高官能度的1,4-苯并二氮杂-5-酮衍生物和相关化合物
2. Highly efficient synthesis of medium-sized lactams via intramolecular Staudinger–aza-Wittig reaction of ω-azido pentafluorophenyl ester: synthesis and biological evaluation of LY411575 analogues [J] . Haruhiko Fuwa, Yumiko Okamura, Yuichi Morohashi, Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2004,第11期

机译：通过ω-叠氮基五氟苯基酯的分子内Staudinger-Aza-Wittig反应高效合成中等大小的内酰胺：LY411575类似物的合成和生物学评估
3. New Efficient Synthesis of 1,4-Benzodiazepin-5-ones by Catalytic Aza-Wittig Reaction [J] . Long Wang, Ru-Qing Qin, Hong-Ye Van, Synthesis: International Journal of Methods in Synthetic Organic Chemistry . 2015,第22期

机译：催化氮杂-维蒂希反应新的高效合成1,4-苯并二氮杂-5-酮
4. Highly Efficient Synthesis of Oxindole Derivatives via Catalytic Intramolecular C-H Insertion Reactions of Diazoamides [C] . Nga Phan-Thi-Thanh, Masaya Tone, Hayato lnoue International Conference on Science and Technology . 2020

机译：通过催化分子内C-H插入式重氮酰胺的催化分子内C-H插入反应高效合成氧吲哚衍生物
5. An application of the intramolecular Heck reaction: A new strategy in the synthesis of Hasubanan alkaloids. Preparation of unsymmetrical biaryls via the Stille cross-coupling reaction: Synthesis of highly functional intermediates towards the synthesis of vindoline. [D] . Frank, Anthony Joseph. 2002

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6. Divergent Stereocontrol of Acid Catalyzed Intramolecular Aldol Reactions of 237-Triketoesters: Synthesis of Highly Functionalized Cyclopentanones [O] . Phong Truong, Charles S. Shanahan, Michael P. Doyle -1

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7. One-Pot Organocatalytic Domino Michael-Aldol and Intramolecular SN2 Reactions. Asymmetric Synthesis of Highly Functionalized Epoxycyclohexanone Derivatives [O] . -1

机译：单盆有机催化多米诺MICHAEL-ALDOL和分子内SN2反应。高官能化环氧环己酮衍生物的不对称合成

Efficient Solid-Phase Synthesis of Highly Functionalized 1,4-Benzodiazepin-5-one Derivatives and Related Compounds by Intramolecular Aza-Wittig Reactions

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