An efficient one-pot decarboxylative aromatization of tetrahydro-b-carbolines by using N-chlorosuccinimide: total synthesis of norharmane, harmane and eudistomins

Ahmed Kamal; Manda Sathish; A. V. G. Prasanthi

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An efficient one-pot decarboxylative aromatization of tetrahydro-b-carbolines by using N-chlorosuccinimide: total synthesis of norharmane, harmane and eudistomins

机译：使用N-氯琥珀酰亚胺，通过N-氯琥珀酰亚胺的一种有效的一罐脱羧芳族化芳族化：Norharmane，Harkane和Eudistomins的总合成

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A facile method for the synthesis of a variety of b-carbolines and their natural products such as norharmane (2a), harmane (2b), eudistomins I, N, T, and U (6, 7, 9 and 10, respectively) has been successfully developed via a decorboxylative aromatization tool by employing N-chlorosuccinimide (NCS) as a mild and efficient reagent. Gratifyingly, this reagent system proceeds in a one-pot manner and converted all the tetrahydro-b-carboline acids into their corresponding decorboxylative aromatic products with good to excellent yields. Additionally, this system works well in the case of tetrahydro-b-carboline esters to produce their aromatic partners in high yields.

机译：用于合成各种B-胶卷的容易方法及其自然产物，如诺汉（2A），气球（2B），Eudistomins I，N，T和U（6,7,9和10）具有通过使用N-氯琥珀酰亚胺（NCS）作为温和和有效的试剂成功开发了柔顶织剂芳族化工具。这种试剂系统以单罐的方式进行，并将所有四氢-B-咔啉酸转化为其相应的柔化芳族产物，良好至优异的产率。另外，该系统在四氢-B-咔啉酯的情况下运行良好，以高产率产生芳香的伴侣。

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《RSC Advances》 |2015年第109期|共6页
作者
Ahmed Kamal; Manda Sathish; A. V. G. Prasanthi;
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作者单位

Medicinal Chemistry &

Pharmacology CSIR-Indian Institute of Chemical Technology Hyderabad 500 007 India.;

Medicinal Chemistry &

Pharmacology CSIR-Indian Institute of Chemical Technology Hyderabad 500 007 India.;

Department of Medicinal Chemistry National Institute of Pharmaceutical Education and Research (NIPER) Hyderabad-500 037 India;

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中图分类化学;
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1. An efficient one-pot decarboxylative aromatization of tetrahydro-b-carbolines by using N-chlorosuccinimide: total synthesis of norharmane, harmane and eudistomins [J] . Ahmed Kamal, Manda Sathish, A. V. G. Prasanthi RSC Advances . 2015,第109期

机译：使用N-氯琥珀酰亚胺，通过N-氯琥珀酰亚胺的一种有效的一罐脱羧芳族化芳族化：Norharmane，Harkane和Eudistomins的总合成
2. Iodine-catalyzed chemoselective dehydrogenation and aromatization of tetrahydro-beta-carbolines: A short synthesis of Kumujian-C, Eudistomin-U, Norharmane, Harmane Harmalan and Isoeudistomine-M [J] . Gaikwad Sunil, Kamble Dayanand, Lokhande Pradeep Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2018,第25期

机译：碘催化的化学选择性脱氢和四氢β-蛋白的芳香化：Kumujian-C，eudistomin-U，Norharmane，Harmalan和Isoeudistomine-M的短合成
3. Application of metal free aromatization to total synthesis of perlolyrin, flazin, eudistomin U and harmane [J] . Santhanam Srinath, Ramu Abinaya, Baburaj Baskar, Journal of Heterocyclic Chemistry: The International Journal of Heterocyclic Chemistry . 2020,第5期

机译：无金属芳族化将金属芳烃化应用于Perlolylin，Flazin，eudistomin U和Harmane的完全合成
4. One-pot synthesis of Corey lactone in 150-minutes and totalsynthesis of latanoprost [C] . Nariyoshi Umekubo, Yujiro Hayashi 日本化学会春季年会 . 2020

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机译：瓜纳卡斯蒂芬A的三环核的合成，烯丙基N-甲苯基氨基甲酸酯的脱羧重排和膦催化的α-氨基烷基亚烷基酯的分子内γ-Umpolung加成，以及（+）-Ibophyllidine的对映选择性全合成。
6. Room-Temperature Aromatization of Tetrahydro-β-Carbolines by 2-Iodoxybenzoic Acid (IBX): Utility in a Total Synthesis of Eudistomin U [O] . Joseph D. Panarese, Stephen P. Waters -1

机译：四氢β咔啉室温芳由2-碘酰基苯甲酸（IBX）：实用中Eudistomin的U一个全合成
7. Meroterpenoid total synthesis: conversion of geraniol and farnesol into amorphastilbol, grifolin and grifolic acid by dioxinone-β-keto-acylation, palladium catalyzed decarboxylative allylic rearrangement and aromatization [O] . Ma, TK, White, AJP, Barrett, AGM 2017

机译：萜类化合物全合成：通过二恶英酮-β-酮 - 酰化，钯催化的脱羧烯丙基重排和芳构化，将香叶醇和法呢醇转化为吗啉噻吩，grifolin和grifolic acid

An efficient one-pot decarboxylative aromatization of tetrahydro-b-carbolines by using N-chlorosuccinimide: total synthesis of norharmane, harmane and eudistomins

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