The asymmetric Bischler–Napieralski reaction: preparation of 1,3,4-trisubstituted 1,2,3,4-tetrahydroisoquinolines

Marcello Nicoletti David OHagan and Alexandra M. Z. Slawin

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The asymmetric Bischler–Napieralski reaction: preparation of 1,3,4-trisubstituted 1,2,3,4-tetrahydroisoquinolines

机译：不对称的Bischler–Napieralski反应：1,3,4-三取代的1,2,3,4-四氢异喹啉的制备

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The Bischler–Napieralski reaction, which is used to prepare dihydroisoquinolines from phenylethylamides, isndemonstrated by the reaction of (S)-1-alkyl-1,2-diphenylethylamides with POCl3–P2O5. The reaction generated 3-nalkyl-4-phenyl-1,2-dihydroisoquinolines with stereochemical selectivities of 80–91% de depending on the alkyl andnthe acetamide substituents. These are the first examples of the asymmetric Bischler–Napieralski reaction wherencyclisation discriminates between two identical diastereotopic aryl groups. Reduction of the resultant dihydroisoquinolinenproducts with LiAlH4 generated the corresponding 1,2,3,4-tetrahydroisoquinolines in a stereoselectivenmanner, carrying three stereogenic centres at C(1), C(3) and C(4).

机译：Bischler–Napieralski反应（用于由苯基乙基酰胺制备二氢异喹啉）由（S）-1-烷基-1，2-二苯基乙基酰胺与POCl3–P2O5的反应证明。反应生成3-正烷基-4-苯基-1，2-二氢异喹啉，其立体化学选择性为80-91％de，具体取决于烷基和乙酰胺取代基。这些是不对称Bischler-Napieralski反应的第一个例子，其中环化作用可区分两个相同的非对映异构芳基。用LiAlH4还原生成的二氢异喹啉烯产物可在立体选择性分子中生成相应的1,2,3,4-四氢异喹啉，在C（1），C（3）和C（4）带有三个立体中心。

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《Journal of the Chemical Society, Perkin Transactions 1》 |2002年第1期|p.116-121|共6页
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Marcello Nicoletti David OHagan and Alexandra M. Z. Slawin;
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University of St. Andrews, School of Chemistry, Centre for Biomolecular Sciences, NorthHaugh, St. Andrews, Fife, UK KY16 9ST. E-mail: do1@st-andrews.ac.uk;

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1. The asymmetric Bischler-Napieralski reaction: preparation of 1,3,4-trisubstituted 1,2,3,4-tetrahydroisoquinolines [J] . Nicoletti M., OHagan D., Slawin AMZ. Journal of the Chemical Society, Perkin Transactions 1 . 2002,第1期

机译：不对称的Bischler-Napieralski反应：1,3,4-三取代的1,2,3,4-四氢异喹啉的制备
2. Flexible Synthesis of Enantiomeric and Racemic 3-Hydroxymethyl-1,2,3,4-tetrahydroisoquinolines via Bischler-Napieralski Reaction [J] . KANG Chuan-qing, DU Zhi-jun, WANG Lan-lan, 高等学校化学研究（英文版） . 2012,第005期

机译：通过Bischler-Napieralski反应灵活合成对映体和外消旋3-羟甲基-1,2,3,4-四氢异喹啉
3. Unexpected PF6 Anion Metathesis during the Bischler–Napieralski Reaction: Synthesis of 3,4-Dihydroisoquinoline Hexafluorophosphates and Their Tetrahydroisoquinoline Related Alkaloids [J] . Carlos E. Puerto Galvis, Mario A. Macías, Vladimir V. Kouznetsov Synthesis: International Journal of Methods in Synthetic Organic Chemistry . 2019,第9期

机译：Bischler-Napieralski反应期间意外的PF6阴离子复分解：合成3,4-二羟基喹啉六氟磷酸盐及其四氢异喹啉相关生物碱
4. Ruthenium-Catalyzed Reaction of l-Cyclopropyl-2-propyn-1-ols with Anilines: A Novel Approach to Preparation of Trisubstituted Conjugated Enynes [C] . Yoshihiro Yamauchi, Gen Onodera, Yoshihiro Miyake Symposium on Organometallic Chemistry . 2006

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5. Dual labeled TIPP (Tyr-Tic-Phe-Phe, Tic = 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid) peptides as pharmacological tools to study delta opioid receptors [D] . Peck, Angela Marie 2007

机译：双标记的TIPP（Tyr-Tic-Phe-Phe，Tic = 1,2,3,4-四氢异喹啉3-羧酸）肽作为研究δ阿片受体的药理学工具
6. Direct Observation of Intermediates Involved in the Interruption of the Bischler–Napieralski Reaction [O] . Kolby L. White, Marius Mewald, Mohammad Movassaghi -1

机译：直接观察涉及Bischler-Napieralski反应中断的中间体
7. Asymmetric Electrophilic alpha-Amidoalkylation, VII1): Generation, Crystal Structure, and Trapping Reactions of a Chiral 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline Derived N-Acyliminium Ion [O] . Wanner Klaus Th., Praschak Ilona, Nagel Ulrich 1990

机译：不对称亲电子α-酰胺基烷基化，VII1）：手性6,7-二甲氧基-1,2,3,4-四氢异喹啉衍生的N-酰基亚胺离子的产生，晶体结构和捕获反应

The asymmetric Bischler–Napieralski reaction: preparation of 1,3,4-trisubstituted 1,2,3,4-tetrahydroisoquinolines

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