diethyl 2,3,5,7,8,9,10,10a-octahydro-1,3-dioxo-2-phenyl-1H-[1,2,4]triazolo[1,2-a]cinnolin-5-ylphosphonate

Base Information

• Chemical Name: diethyl 2,3,5,7,8,9,10,10a-octahydro-1,3-dioxo-2-phenyl-1H-[1,2,4]triazolo[1,2-a]cinnolin-5-ylphosphonate
• CAS No.: 1417995-25-5
• Molecular Formula: C₂₀H₂₆N₃O₅P
• Molecular Weight: 419.417

Synonyms:diethyl 2,3,5,7,8,9,10,10a-octahydro-1,3-dioxo-2-phenyl-1H-[1,2,4]triazolo[1,2-a]cinnolin-5-ylphosphonate

Chemical Property of diethyl 2,3,5,7,8,9,10,10a-octahydro-1,3-dioxo-2-phenyl-1H-[1,2,4]triazolo[1,2-a]cinnolin-5-ylphosphonate

Chemical Property:

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Technology Process of diethyl 2,3,5,7,8,9,10,10a-octahydro-1,3-dioxo-2-phenyl-1H-[1,2,4]triazolo[1,2-a]cinnolin-5-ylphosphonate

There total 3 articles about diethyl 2,3,5,7,8,9,10,10a-octahydro-1,3-dioxo-2-phenyl-1H-[1,2,4]triazolo[1,2-a]cinnolin-5-ylphosphonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 53.0%

4-Phenyl-1,2,4-triazolidine-3,5-dione (4233-33-4) + (E)-diethyl cyclohex-2-enylidenemethylphosphonate (78463-01-1) → diethyl 2,3,5,7,8,9,10,10a-octahydro-1,3-dioxo-2-phenyl-1H-[1,2,4]triazolo[1,2-a]cinnolin-5-ylphosphonate (1417995-25-5)

Guidance literature:

In 1,2-dichloro-ethane; for 1h; Reflux; Inert atmosphere;

DOI:10.1016/j.tet.2012.11.059

Reference yield:

Tetraethyl methylenediphosphonate (1660-94-2) → diethyl 2,3,5,7,8,9,10,10a-octahydro-1,3-dioxo-2-phenyl-1H-[1,2,4]triazolo[1,2-a]cinnolin-5-ylphosphonate (1417995-25-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / toluene / 0.25 h / 20 °C / Inert atmosphere

1.2: 2 h / 20 °C / Inert atmosphere

2.1: 1,2-dichloro-ethane / 1 h / Reflux; Inert atmosphere

With sodium hydride; In 1,2-dichloro-ethane; toluene; 1.2: |Horner-Wadsworth-Emmons Olefination / 2.1: |Diels-Alder Cycloaddition;

DOI:10.1016/j.tet.2012.11.059

Reference yield:

1-cyclohexene-1-carboxaldehyde (1192-88-7) → diethyl 2,3,5,7,8,9,10,10a-octahydro-1,3-dioxo-2-phenyl-1H-[1,2,4]triazolo[1,2-a]cinnolin-5-ylphosphonate (1417995-25-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / toluene / 0.25 h / 20 °C / Inert atmosphere

1.2: 2 h / 20 °C / Inert atmosphere

2.1: 1,2-dichloro-ethane / 1 h / Reflux; Inert atmosphere

With sodium hydride; In 1,2-dichloro-ethane; toluene; 1.2: |Horner-Wadsworth-Emmons Olefination / 2.1: |Diels-Alder Cycloaddition;

DOI:10.1016/j.tet.2012.11.059

upstream raw materials:

Tetraethyl methylenediphosphonate

4-Phenyl-1,2,4-triazolidine-3,5-dione

(E)-diethyl cyclohex-2-enylidenemethylphosphonate

1-cyclohexene-1-carboxaldehyde

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