A Practical Synthesis of 5-Substituted 1H-Tetrazoles from Aldoximes Employing the Azide Anion from Diphenyl Phosphorazidate

5-Substituted 1H-tetrazoles were effectively synthesized from aldoximes and diphenyl phosphorazidate (DPPA) under reflux conditions in xylenes. Various aldoximes underwent the cycloaddition reaction to afford the corresponding 5-substituted 1H-tetrazoles in short reaction times and in good yields. Chiral aldoximes derived from amino acids also gave aminotetrazoles with almost no racemization.

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Ti-Catalyzed Enantioselective Addition of Cyanide to Imines. A Practical Synthesis of Optically Pure α-Amino Acids

Journal of the American Chemical Society ◽

10.1021/ja9840605 ◽

1999 ◽

Vol 121 (17) ◽

pp. 4284-4285 ◽

Cited By ~ 166

Author(s):

Clinton A. Krueger ◽

Kevin W. Kuntz ◽

Carolyn D. Dzierba ◽

Wolfgang G. Wirschun ◽

John D. Gleason ◽

...

Keyword(s):

Amino Acids ◽

Practical Synthesis ◽

Enantioselective Addition ◽

Optically Pure

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ChemInform Abstract: Practical Synthesis of Optically Active α-Hydrazino Acids from α-Amino Acids.

ChemInform ◽

10.1002/chin.198733314 ◽

1987 ◽

Vol 18 (33) ◽

Author(s):

J. VIRET ◽

J. GABARD ◽

A. COLLET

Keyword(s):

Amino Acids ◽

Optically Active ◽

Practical Synthesis

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Advance synthetic approaches to 1,2,3-triazole derived compounds: State of art 2004-2020

Current Organocatalysis ◽

10.2174/2213337208666210428123033 ◽

2021 ◽

Vol 08 ◽

Author(s):

Adarsh Sahu

Keyword(s):

Structural Characteristics ◽

Cycloaddition Reaction ◽

Reaction Times ◽

Synthetic Methods ◽

Environmentally Benign ◽

Future Directions ◽

Triazole Derivatives ◽

The Past ◽

Synthetic Approaches ◽

Reaction Profile

Background: 1,2,3-triazole is considered widely explored scaffolds by medicinal chemists because of their therapeutic importance. The structural characteristics of 1,2,3-triazoles allow this to mimic certain functional groups demonstrating its utility to prepare new medicinal compounds using the concept of bioisosterism and molecular hybridization. Centered on Huisgens cycloaddition reaction, over the past decade and a half, click chemistry approaches were developed to furnish triazole derivatives with various applications ranging from drugs to bioconjugation linkers. Objective: In the present review, we aim to highlight the different approaches developed for the synthesis of 1,2,3-triazole derivatives and in particular advances in synthetic methods for the last 16 years. This review is also intended to help researchers for finding potential future directions and scope in the development of synthetic strategies. Conclucion: As summarized through the compilation of recent advances for 1,2,3-triazole synthesis, it is clear that these protocols have numerous advantages such as cleaner reaction profile, shorter reaction times, excellent product yields, environmentally benign milder reactions, and safe operations.

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Novel Asymmetric Phase-Transfer Catalysts for Practical Synthesis of Unnatural Amino Acids

Asymmetric Organocatalysis 2 ◽

10.1055/sos-sd-205-00613 ◽

2012 ◽

pp. 1

Author(s):

K. Izawa ◽

T. Torii ◽

T. Nishikawa ◽

H. Imai

Keyword(s):

Amino Acids ◽

Unnatural Amino Acids ◽

Phase Transfer ◽

Phase Transfer Catalysts ◽

Practical Synthesis

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A class of α-amino acids-derived multifunctional amidophosphane precatalysts: application to the highly enantio- and diastereoselective silver(I)-catalyzed 1,3-dipolar cycloaddition reaction

Tetrahedron Asymmetry ◽

10.1016/j.tetasy.2017.05.014 ◽

2017 ◽

Vol 28 (7) ◽

pp. 930-938 ◽

Cited By ~ 6

Author(s):

Yihui Hou ◽

Zhipeng Zhou ◽

Pingle Liu ◽

Jiankang Wang ◽

Qinglin Hou ◽

...

Keyword(s):

Amino Acids ◽

Cycloaddition Reaction ◽

Dipolar Cycloaddition

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One-Pot Synthesis of α-Substituted Acrylates

SynOpen ◽

10.1055/s-0037-1610357 ◽

2018 ◽

Vol 02 (02) ◽

pp. 0161-0167

Author(s):

Magdalini Matziari ◽

Yixin Xie

Keyword(s):

Amino Acids ◽

Reaction Times ◽

Synthetic Method ◽

One Pot ◽

Biologically Relevant ◽

Mild Conditions ◽

One Pot Synthesis ◽

Acrylic Esters ◽

Natural Amino Acids ◽

Work Up

A simple and efficient synthetic method towards α-substituted acrylic esters has been developed using the Horner–Wadsworth–Emmons (HWE) reaction with HCHO after alkylation of phosphonoacetates in a one-pot reaction. This method allows the smooth introduction of various side-chains, such as natural amino acids and other biologically relevant substituents. The use of mild conditions, inexpensive reagents, short reaction times and simple work-up and purification steps provides an effective and general alternative to cumbersome multistep and low-yielding procedures described to date.

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