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Literature DB >> 17629296

N,N'-ditosylhydrazine: a convenient reagent for facile synthesis of diazoacetates.

Tatsuya Toma¹, Jun Shimokawa, Tohru Fukuyama.

Abstract

A novel entry to the synthesis of diazoacetates is disclosed. A variety of diazoacetates were synthesized from the corresponding bromoacetates by treatment with N,N'-ditosylhydrazine in moderate to high yields. Ease of operation with the stable crystalline reagent as well as a short reaction time offer a useful alternative to the conventional methods.

Entities: Chemical

Mesh：

Substances：

Year: 2007 PMID： 17629296 DOI： 10.1021/ol701432k

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

14 in total

1. Synthesis of substituted pyrazoles via tandem cross-coupling/electrocyclization of enol triflates and diazoacetates.

Authors: David J Babinski; Hector R Aguilar; Raymond Still; Doug E Frantz
Journal: J Org Chem Date: 2011-06-27 Impact factor: 4.354

2. Asymmetric Formal Total Synthesis of the Stemofoline Alkaloids: The Evolution, Development and Application of a Catalytic Dipolar Cycloaddition Cascade.

Authors: Charles S Shanahan; Chao Fang; Daniel H Paull; Stephen F Martin
Journal: Tetrahedron Date: 2013-09-09 Impact factor: 2.457

3. Stereoselective preparation of cyclobutanes with four different substituents: total synthesis and structural revision of pipercyclobutanamide A and piperchabamide G.

Authors: Renhe Liu; Min Zhang; Thomas P Wyche; Gabrielle N Winston-McPherson; Tim S Bugni; Weiping Tang
Journal: Angew Chem Int Ed Engl Date: 2012-06-19 Impact factor: 15.336

4. tert-Butyl 4-(2-diazo-acet-yl)piperazine-1-carboxyl-ate.

Authors: Asmund Kaupang; Carl Henrik Görbitz; Tore Hansen
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-05-08

5. Coupling of acceptor-substituted diazo compounds and tertiary thioamides: synthesis of enamino carbonyl compounds and their pharmacological evaluation.

Authors: Jim Secka; Arpan Pal; Francis A Acquah; Blaine H M Mooers; Anand B Karki; Dania Mahjoub; Mohamed K Fakhr; David R Wallace; Takuya Okada; Naoki Toyooka; Adama Kuta; Naga Koduri; Deacon Herndon; Kenneth P Roberts; Zhiguo Wang; Bethany Hileman; Nisha Rajagopal; Syed R Hussaini
Journal: RSC Adv Date: 2022-07-05 Impact factor: 4.036

10. α-Bromodiazoacetamides - a new class of diazo compounds for catalyst-free, ambient temperature intramolecular C-H insertion reactions.

Authors: Asmund Kaupang; Tore Bonge-Hansen
Journal: Beilstein J Org Chem Date: 2013-07-11 Impact factor: 2.883

N,N'-ditosylhydrazine: a convenient reagent for facile synthesis of diazoacetates.

1. Synthesis of substituted pyrazoles via tandem cross-coupling/electrocyclization of enol triflates and diazoacetates.

2. Asymmetric Formal Total Synthesis of the Stemofoline Alkaloids: The Evolution, Development and Application of a Catalytic Dipolar Cycloaddition Cascade.

3. Stereoselective preparation of cyclobutanes with four different substituents: total synthesis and structural revision of pipercyclobutanamide A and piperchabamide G.

4. tert-Butyl 4-(2-diazo-acet-yl)piperazine-1-carboxyl-ate.

5. Coupling of acceptor-substituted diazo compounds and tertiary thioamides: synthesis of enamino carbonyl compounds and their pharmacological evaluation.

6. Imidazotetrazines as Weighable Diazomethane Surrogates for Esterifications and Cyclopropanations.

7. Copper-catalyzed [1,2]-rearrangements of allylic iodides and aryl α-diazoacetates.

8. 2-Diazo-1-(1,1-dioxothio-morpholin-4-yl)ethanone.

9. 1,4-Bis(2-diazo-acet-yl)piperazine.

10. α-Bromodiazoacetamides - a new class of diazo compounds for catalyst-free, ambient temperature intramolecular C-H insertion reactions.