scholarly journals Transformation of 2H-1,2,3-benzothiadiazine 1,1-dioxides variously substituted at the aromatic ring, via nucleophilic substitution and demethylation reactions

2020 ◽  
Author(s):  
Imre Gyűjtő ◽  
Márta Porcs-Makkay ◽  
Ernák Ferenc Várda ◽  
Gyöngyvér Pusztai ◽  
Gábor Tóth ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Functional Groups ◽  
Aromatic Ring ◽  
Methoxy Group ◽  
Medicinal Chemistry ◽  
Building Blocks ◽  
Chlorine Atoms ◽  
New Methods ◽  
Pharmacological Interest

2H‑1,2,3‑Benzothiadiazine 1,1-dioxides are a class of compounds of pharmacological interest. After earlier studies carried out at our laboratory on various transformations (alkylation, acylation, reduction) at the hetero ring, the present manuscript focuses on the transformation of substituents at the aromatic carbocycle, including nucleophilic substitution of chlorine atoms and demethylation of the methoxy group with amines. The new methods described here allow the introduction of versatile functional groups on the aromatic ring, making these compounds useful building blocks for organic and medicinal chemistry applications.

scholarly journals Generation and application of Cu-bound alkyl nitrene for the catalyst-controlled synthesis of cyclic β-amino acids

2021 ◽  
Author(s):  
Raj K Tak ◽  
Fuyuki Amemiya ◽  
Hidetoshi Noda ◽  
Masakatsu Shibasaki
Keyword(s):  
Amino Acids ◽  
Medicinal Chemistry ◽  
Building Blocks ◽  
Controlled Synthesis ◽  
New Methods

The advent of saturated N-heterocycles as valuable building blocks in medicinal chemistry has led to the development of new methods to construct such nitrogen-containing cyclic frameworks. Despite the apparent strategic...

Cascade CuH-Catalyzed Conversion of Alkynes to Enantioenriched 1,1-Disubstituted Products

2019 ◽  
Author(s):  
De-Wei Gao ◽  
Yang Gao ◽  
Huiling Shao ◽  
Tian-Zhang Qiao ◽  
Xin Wang ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Medicinal Chemistry ◽  
Proteasome Inhibitors ◽  
Building Blocks ◽  
Unique Role ◽  
Efficient Strategy ◽  
Carbon Centers ◽  
Rapid Access ◽  
Cascade Catalysis ◽  
Privileged Scaffolds

Enantioenriched <i>α</i>-aminoboronic acids play a unique role in medicinal chemistry and have emerged as privileged pharmacophores in proteasome inhibitors. Additionally, they represent synthetically useful chiral building blocks in organic synthesis. Recently, CuH-catalyzed asymmetric alkene hydrofunctionalization has become a powerful tool to construct stereogenic carbon centers. In contrast, applying CuH cascade catalysis to achieve reductive 1,1-difunctionalization of alkynes remains an important, but largely unaddressed, synthetic challenge. Herein, we report an efficient strategy to synthesize <i>α</i>-aminoboronates <i>via </i>CuH-catalyzed hydroboration/hydroamination cascade of readily available alkynes. Notably, this transformation selectively delivers the desired 1,1-heterodifunctionalized product in favor of alternative homodifunctionalized, 1,2-heterodifunctionalized, or reductively monofunctionalized byproducts, thereby offering rapid access to these privileged scaffolds with high chemo-, regio- and enantioselectivity.<br>

A Practical and General Approach to the Late-Stage Functionalization of Complex Sulfonamides

2019 ◽  
Author(s):  
Patrick Fier ◽  
Kevin M. Maloney
Keyword(s):  
Functional Groups ◽  
Late Stage ◽  
Building Blocks ◽  
Pharmaceutical Compounds ◽  
Stage Conversion

Herein we describe the development and application of a method for the mild, late-stage conversion of primary sulfonamides to several other other functional groups. These reactions occur via initial reductive deamination of sulfonamides to sulfinates via an NHC-catalyzed reaction of transiently formed <i>N</i>-sulfonylimines. The method described here is tolerant of nearly all common functional groups, as exemplified by the late-stage derivatization of several complex pharmaceutical compounds. Based on the prevalence of sulfonamide-containing drugs and building blocks, we have developed a method to enable sulfonamides to be applied as versatile synthetic handles for synthetic chemsitry.

A Practical and General Approach to the Late-Stage Functionalization of Complex Sulfonamides

2019 ◽  
Author(s):  
Patrick Fier ◽  
Kevin M. Maloney
Keyword(s):  
Functional Groups ◽  
Late Stage ◽  
Building Blocks ◽  
Pharmaceutical Compounds ◽  
Stage Conversion

Herein we describe the development and application of a method for the mild, late-stage conversion of primary sulfonamides to several other other functional groups. These reactions occur via initial reductive deamination of sulfonamides to sulfinates via an NHC-catalyzed reaction of transiently formed <i>N</i>-sulfonylimines. The method described here is tolerant of nearly all common functional groups, as exemplified by the late-stage derivatization of several complex pharmaceutical compounds. Based on the prevalence of sulfonamide-containing drugs and building blocks, we have developed a method to enable sulfonamides to be applied as versatile synthetic handles for synthetic chemsitry.

Recent Development in the Chemistry of Bicyclic 6+5 Systems, Part II: Chemistry of Triazolopyrimidine Derivatives

2020 ◽  
Vol 17 (12) ◽  
pp. 897-925 ◽  
Author(s):  
Moustafa A. Gouda ◽  
Ameen Ali Abu-Hashem ◽  
Hoda Abdel Raouf Hussein ◽  
Ahmed S. Aly
Keyword(s):  
Heterocyclic Compounds ◽  
Building Blocks ◽  
Pharmacological Interest

This review describes the synthesis and reactions of substituted triazolopyrimidines as building blocks toward polyfunctionalized heterocyclic compounds with pharmacological interest.

scholarly journals PyroMEMS as Future Technological Building Blocks for Advanced Microenergetic Systems

Micromachines ◽  
2021 ◽  
Vol 12 (2) ◽  
pp. 118
Author(s):  
Jean-Laurent Pouchairet ◽  
Carole Rossi
Keyword(s):  
Building Block ◽  
Building Blocks ◽  
Small Scale ◽  
Technological Evolution ◽  
Research Groups ◽  
Function Block ◽  
The Past ◽  
New Methods ◽  
Safety And Reliability ◽  
Electronically Controllable

For the past two decades, many research groups have investigated new methods for reducing the size and cost of safe and arm-fire systems, while also improving their safety and reliability, through batch processing. Simultaneously, micro- and nanotechnology advancements regarding nanothermite materials have enabled the production of a key technological building block: pyrotechnical microsystems (pyroMEMS). This building block simply consists of microscale electric initiators with a thin thermite layer as the ignition charge. This microscale to millimeter-scale addressable pyroMEMS enables the integration of intelligence into centimeter-scale pyrotechnical systems. To illustrate this technological evolution, we hereby present the development of a smart infrared (IR) electronically controllable flare consisting of three distinct components: (1) a controllable pyrotechnical ejection block comprising three independently addressable small-scale propellers, all integrated into a one-piece molded and interconnected device, (2) a terminal function block comprising a structured IR pyrotechnical loaf coupled with a microinitiation stage integrating low-energy addressable pyroMEMS, and (3) a connected, autonomous, STANAG 4187 compliant, electronic sensor arming and firing block.

scholarly journals Non-Enzymatic Desymmetrization Reactions in Aqueous Media

Symmetry ◽  
2021 ◽  
Vol 13 (4) ◽  
pp. 720
Author(s):  
Satomi Niwayama
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Functional Groups ◽  
Organic Compounds ◽  
Recent Progress ◽  
Aqueous Media ◽  
Building Blocks ◽  
Organic Reactions ◽  
Environmentally Benign ◽  
Enzymatic Desymmetrization

Symmetric organic compounds are generally obtained inexpensively, and therefore they can be attractive building blocks for the total synthesis of various pharmaceuticals and natural products. The drawback is that discriminating the identical functional groups in the symmetric compounds is difficult. Water is the most environmentally benign and inexpensive solvent. However, successful organic reactions in water are rather limited due to the hydrophobicity of organic compounds in general. Therefore, desymmetrization reactions in aqueous media are expected to offer versatile strategies for the synthesis of a variety of significant organic compounds. This review focuses on the recent progress of desymmetrization reactions of symmetric organic compounds in aqueous media without utilizing enzymes.

An Efficient Substrate-Induced Method for the Synthesis of CF3-Substituted Cyclopropanes by Metal-Free Reaction of Trifluoromethyl Styrylisoxazoles with Nitromethane

Synthesis ◽  
2020 ◽  
Author(s):  
Feng Li ◽  
Hai Ma ◽  
Qing-he Zhao ◽  
Guang-hao Yu ◽  
Ye-chen Meng ◽  
...  
Keyword(s):  
Functional Groups ◽  
Phase Transfer ◽  
Cyclization Reaction ◽  
Metal Free ◽  
Tert Butyl ◽  
Pharmacological Interest ◽  
Substituted Cyclopropanes

AbstractA series of (trifluoromethyl)cyclopropanes (TFCPs) tolerating a broad range of functional groups, known as tert-butyl bioisosteres, have been obtained from the cyclization reaction between nitromethane­ and 5-[β-(trifluoromethyl)styryl]isoxazoles in 70–94% yields and 75:25 to 90:10 dr. This method offers practical access to this cyclopropyl moiety of pharmacological interest, employing an inorganic base under phase-transfer conditions.

scholarly journals Janus All‐Cis 2,3,4,5,6‐Pentafluorocyclohexyl Building Blocks Applied to Medicinal Chemistry and Bioactives Discovery Chemistry

2021 ◽  
Author(s):  
Joshua L. Clark ◽  
Rifahath M. Neyyappadath ◽  
Cihang Yu ◽  
Alexandra M. Z. Slawin ◽  
David B. Cordes ◽  
...  
Keyword(s):  
Medicinal Chemistry ◽  
Building Blocks

Direct amidation of acid fluorides using germanium amides

2021 ◽  
Author(s):  
Ardalan Hayatifar ◽  
Emily Elifritz ◽  
Molly Bloom ◽  
Kaitlyn Pixley ◽  
Chris Fennell ◽  
...  
Keyword(s):  
Functional Groups ◽  
New Method ◽  
New Methods ◽  
Acid Fluorides ◽  
Direct Amidation

Amide functional groups are an essential linkage that are found in peptides, proteins, and pharmaceuticals and new methods are constantly being sought for their formation. Here, a new method is...

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