4.7 Article

Synthesis of Tryptamines from Radical Cyclization of 2-Iodoaryl Allenyl Amines and Coupling with 2-Azallyls

Related references

Note: Only part of the references are listed.
Article Chemistry, Organic

Super-Electron-Donor 2-Azaallyl Anions Enable Construction of Isoquinolines

Quanxing Zi et al.

Summary: This study introduces a transition-metal-free method using superelectron-donor for the rapid construction of isoquinolines through a tandem reaction, demonstrating high yields and good functional group tolerance of the method. Additionally, a gram scale synthesis confirms the scalability of the approach.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Transition-Metal-Free C(sp3)-H Coupling of Cycloalkanes Enabled by Single-Electron Transfer and Hydrogen Atom Transfer

Linlin Zhang et al.

Summary: A unique transition-metal-free C(sp(3))-H/C(sp(3))-H coupling of cycloalkanes at room temperature is reported, where unactivated cycloalkanes and 2-azaallyls underwent a combination process of single-electron transfer (SET) and hydrogen atom transfer (HAT) to deliver a variety of functionalized products. This expedient approach enables the coupling of cycloalkanes under mild conditions without transition metals, initiators, and oxidants.

ORGANIC LETTERS (2021)

Article Chemistry, Multidisciplinary

Design and Synthesis of Fluorescent 1,3-Diaryl-β-carbolines and 1,3-Diaryl-3,4-dihydro-β-carbolines

JiYang Pu et al.

Summary: The study synthesized 1,3-diaryl-beta-carboline derivatives with unique optical properties, showing strong emission in the range of 387-409 nm and high photoluminescence quantum yields of up to 74%. Density functional theory calculations were conducted to better understand the geometric, electronic, and optical properties of these novel compounds.

ACS OMEGA (2021)

Article Chemistry, Multidisciplinary

Synthesis of an elusive, stable 2-azaallyl radical guided by electrochemical and reactivity studies of 2-azaallyl anions

Grace B. Panetti et al.

Summary: The super electron donor ability of 2-azaallyl anions has been discovered and applied in various reactions, while the redox properties of these species have been rarely studied. Electrochemical analysis revealed an oxidation wave at -1.6 V versus Fc/Fc(+), lower than the predicted potential, and led to the design of the first stable acyclic 2-azaallyl radical. These findings highlight the importance of reorganization energy in the development of potent organic reductants.

CHEMICAL SCIENCE (2021)

Review Chemistry, Multidisciplinary

The Persistent Radical Effect in Organic Synthesis

Dirk Leifert et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Amino Acid Schiff Base Bearing Benzophenone Imine As a Platform for Highly Congested Unnatural α-Amino Acid Synthesis

Yohei Matsumoto et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Synthesis of Indoles through Domino Reactions of 2-Fluorotoluenes and Nitriles

Jianyou Mao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Synthesis of Benzofuran Derivatives through Cascade Radical Cyclization/Intermolecular Coupling of 2-Azaallyls

Guogang Deng et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Medicinal

Identification of a Potent Tryptophan-Based TRPM8 Antagonist With in Vivo Analgesic Activity

Alessia Bertamino et al.

JOURNAL OF MEDICINAL CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

Iodospirocyclization of Tryptamine-Derived Isocyanides: Formal Total Synthesis of Aspidofractinine

Jordy M. Saya et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Review Chemistry, Multidisciplinary

2-Azaallyl Anions, 2-Azaallyl Cations, 2-Azaallyl Radicals, and Azomethine Ylides

Shaojian Tang et al.

CHEMICAL REVIEWS (2018)

Article Plant Sciences

Bioactivity-guided synthesis of gramine derivatives as new MT1 and 5-HT1A receptors agonists

Xiu-Juan Yin et al.

JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH (2017)

Article Chemistry, Multidisciplinary

Transition-metal-free chemo- and regioselective vinylation of azaallyls

Minyan Li et al.

NATURE CHEMISTRY (2017)

Article Chemistry, Organic

Selenium-Iodine Cooperative Catalyst for Chlorocyclization of Tryptamine Derivatives

Takahiro Horibe et al.

ORGANIC LETTERS (2017)

Article Chemistry, Multidisciplinary

Concise Total Syntheses of (+)-Haplocidine and (+)-Haplocine via Late-Stage Oxidation of (+)-Fendleridine Derivatives

Kolby L. White et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Organic

Synthesis of the Azepinobisindole Alkaloid Iheyamine A Enabled by a Cross-Mannich Reaction

Ashley C. Lindsay et al.

ORGANIC LETTERS (2016)

Article Chemistry, Organic

C3 Alkylation of Indoles Catalyzed by Carbocations under Continuous-Flow Conditions

Li Wan et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2016)

Article Chemistry, Medicinal

Structure-Activity Relationships of Novel Tryptamine-Based Inhibitors of Bacterial Transglycosylase

Izidor Sosic et al.

JOURNAL OF MEDICINAL CHEMISTRY (2015)

Article Chemistry, Organic

Copper-Catalyzed Direct C2-Benzylation of Indoles with Alkylarenes

Hui-Jun Zhang et al.

JOURNAL OF ORGANIC CHEMISTRY (2015)

Article Chemistry, Analytical

Enzymatic synthesis of tryptamine and its halogen derivatives selectively labeled with hydrogen isotopes

Sylwia Dragulska et al.

JOURNAL OF RADIOANALYTICAL AND NUCLEAR CHEMISTRY (2014)

Article Chemistry, Organic

Synthesis of Tryptamine Derivatives via a Direct, One-Pot Reductive Alkylation of Indoles

Marika Righi et al.

JOURNAL OF ORGANIC CHEMISTRY (2012)

Article Chemistry, Multidisciplinary

Total Synthesis Guided Structure Elucidation of (+)-Psychotetramine

Klement Foo et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Review Chemistry, Multidisciplinary

Marine Indole Alkaloids: Potential New Drug Leads for the Control of Depression and Anxiety

Anna J. Kochanowska-Karamyan et al.

CHEMICAL REVIEWS (2010)

Article Chemistry, Multidisciplinary

New Synthetic Technologies for the Construction of Heterocycles and Tryptamines

K. C. Nicolaou et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

Article Chemistry, Organic

Stereoselective oxidative rearrangement of 2-aryl tryptamine derivatives

Mohammad Movassaghi et al.

ORGANIC LETTERS (2008)