Enantioselective Synthesis of Hydantoin and Diketopiperazine-Fused Tetrahydroisoquinolines via Pictet-Spengler Reaction

Liu Shih-I; Haung Jia-Yun; Barve Indrajeet J.; Huang Sheng-Cih; Sun Chung-Ming

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Enantioselective Synthesis of Hydantoin and Diketopiperazine-Fused Tetrahydroisoquinolines via Pictet-Spengler Reaction

机译：乙藻和二酮哌嗪 - 融合四氢异喹啉的致注重辅助合成 - Spengler反应

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摘要

An enantioselective synthesis of iso-, isothio-, and isoselenohydantoin and diketopiperazine-fused tetrahydroisoquinolines from L-Dopa was reported. The route consists of an Pictet-Spengler reaction of (S)-2-amino-3-(3,4-dimethoxyphenyl)propanoates with various aldehydes to afford diastereomeric tetrahydroisoquinolines. Next step, the tetrahydroisoquinolines were further reacted with iso-, isothio-, or isoselenocyanates to construct hydantoin. Similarly, the diketopiperazine moiety was constructed by subjecting tetrahydroisoquinolines to a condensation reaction with chloroacetyl chloride followed by nucleophilic addition with various primary amines.

机译：据报道了来自L-DOPA的iso-，异硫酸和伊索伦洛霉素和二酮哌嗪稠合的四氢异喹啉的对映选择性合成。该路线由（S）-2-氨基-3-（3,4-二甲氧基苯基）丙烷丙氨酸的丙甲酯 - Spengler反应组成，具有各种醛，得到非对映氨基四羟基异喹啉。下一步骤，将四氢异喹啉与异，异噻唑或异糖蛋白硅酸酯进一步反应以构建乙烃。类似地，通过使四氢异喹啉对氯乙酰氯进行缩合反应，然后用各种伯胺进行亲核来构建二酮哌嗪部分。

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来源
《ACS combinatorial science》 |2019年第4期|共9页
作者
Liu Shih-I; Haung Jia-Yun; Barve Indrajeet J.; Huang Sheng-Cih; Sun Chung-Ming;
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作者单位

Natl Chiao Tung Univ Dept Appl Chem Hsinchu 300 Taiwan;

Natl Chiao Tung Univ Dept Appl Chem Hsinchu 300 Taiwan;

Natl Chiao Tung Univ Dept Appl Chem Hsinchu 300 Taiwan;

Natl Chiao Tung Univ Dept Appl Chem Hsinchu 300 Taiwan;

Natl Chiao Tung Univ Dept Appl Chem Hsinchu 300 Taiwan;

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原文格式 PDF
正文语种 eng
中图分类化学;
关键词
enantioselective synthesis; diketopiperazine-fused tetrahydroisoquinolines; hydantoin-fused tetrahydroisoquinolines; molecular hybridization; Pictet-Spengler reaction;

机译：对映选择性合成;Diketopiperazine融合的四氢异喹啉;乙内蛋白稠合四氢异喹啉;分子杂交;Pictet-Spengler反应;

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1. Enantioselective Synthesis of Hydantoin and Diketopiperazine-Fused Tetrahydroisoquinolines via Pictet-Spengler Reaction [J] . Liu Shih-I, Haung Jia-Yun, Barve Indrajeet J., ACS combinatorial science . 2019,第4期

机译：乙藻和二酮哌嗪 - 融合四氢异喹啉的致注重辅助合成 - Spengler反应
2. A variation of the Pictet-Spengler reaction via a sequential reduction-cyclization reaction of N-acylcarbamates: synthesis of 1-substituted tetrahydroisoquinoline derivatives [J] . Chutima Kuhakarn, Nattakan Panyachariwat, Somsak Ruchirawat Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2007,第46期

机译：N-酰基氨基甲酸酯的顺序还原环化反应引起的Pictet-Spengler反应的变化：1-取代的四氢异喹啉衍生物的合成
3. Solid-phase synthesis of tetrahydro-beta-carbolines and tetrahydroisoquinolines by stereoselective intramolecular n-carbamyliminium Pictet-Spengler reactions [J] . Diness F, Beyer J, Meldal M Chemistry: A European journal . 2006,第31期

机译：立体选择性分子内n-氨基甲酰基亚胺Pictet-Spengler反应固相合成四氢-β-咔啉和四氢异喹啉
4. Enantioselective Synthesis of Spirooxindoles via Pictet-Spengler, Oxidative and Wagner-Meerwein Rearrangements of Isotryptamine [C] . Naoki Matsuyama, Masaru Kondo, Shinobu Takizawa 日本化学会春季年会講演予稿集 . 2018

机译：纤维毒素纤维素吲哚替昔林醛，氧化性和瓦格纳 - Meerwein重排酶的联系合成
5. I. Enantioselective total synthesis of quinine and quinidine. II. Thiourea-catalyzed enantioselective C-C bond-forming reactions. a. Catalytic asymmetric N-acyliminium ion cyclizations. b. Catalytic asymmetric aza-Baylis-Hillman reactions [D] . Raheem, Izzat Tiedje 2008

机译：I.奎宁和奎尼丁的对映选择性全合成。二。硫脲催化的对映选择性C-C键形成反应。一个。催化不对称N-酰亚胺离子环化。 b。催化不对称氮杂-Baylis-Hillman反应
6. Enantioselective Pictet-Spengler Reactions of Isatins for the Synthesis of Spiroindolones [O] . Joseph J. Badillo, Abel Silva-García, Benjamin H. Shupe, -1

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7. First synthesis of (R)- and (S)-1,2,3,4-tetrahydroisoquinoline-3-phosphonic acid (TicP) using a pictet-spengler reaction [O] . Viveros-Ceballos José Luis, Ordóñez Mario, Sayago Francisco J., 2017

机译：使用皮克特-斯彭格勒反应首次合成（R）-和（S）-1,2,3,4-四氢异喹啉-3-膦酸（TicP）

Enantioselective Synthesis of Hydantoin and Diketopiperazine-Fused Tetrahydroisoquinolines via Pictet-Spengler Reaction

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