ChemInform Abstract: SYNTHESIS OF DIMETHYL 1,2‐DIHYDROPYRIDAZINE‐1,2‐DICARBOXYLATE

Altman, Lawrence J.; Semmelhack, M. F.; Hornby, R.; Vederas, John C.

doi:10.1002/chin.197537255

Chemischer Informationsdienst

1975

DOI: 10.1002/chin.197537255

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ChemInform Abstract: SYNTHESIS OF DIMETHYL 1,2‐DIHYDROPYRIDAZINE‐1,2‐DICARBOXYLATE

Lawrence J. Altman¹,

M. F. Semmelhack²,

R. Hornby³

et al.

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2023

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“…This reaction required careful optimization of temperature and duration to achieve high yields due to competitive product decomposition (see Supporting Information). Irradiation of 13 with 350 nm light resulted in 4π electrocyclic closure to 8a in 71% yield according to the report by Altman 21 and Coote. 19c We performed this two-step sequence routinely on multigram scale.…”

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confidence: 57%

A Metal-Free Cyclobutadiene Reagent for Intermolecular [4 + 2] Cycloadditions

et al. 2023

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Cyclobutadiene is a highly reactive antiaromatic hydrocarbon that has fascinated chemists for over 60 years. However, its preparation and uses in chemical synthesis are sparing, in part due to its lengthy synthesis that generates hazardous byproducts including excess heavy metals. Herein, we report a scalable, metal-free cyclobutadiene reagent, diethyldiazabicyclohexene dicarboxylate, and explore its intermolecular [4 + 2] cycloaddition with various electron-deficient alkenes. We also demonstrate its utility in a three-step synthesis of dipiperamide G and a diverse array of product derivatizations including bromocyclobutadiene.

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confidence: 57%

A Metal-Free Cyclobutadiene Reagent for Intermolecular [4 + 2] Cycloadditions

et al. 2023

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ChemInform Abstract: SYNTHESIS OF DIMETHYL 1,2‐DIHYDROPYRIDAZINE‐1,2‐DICARBOXYLATE

Cited by 1 publication

References 1 publication

A Metal-Free Cyclobutadiene Reagent for Intermolecular [4 + 2] Cycloadditions

A Metal-Free Cyclobutadiene Reagent for Intermolecular [4 + 2] Cycloadditions

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