2-(1-cyano-2-phenylvinyl)-5-(ethoxycarbonyl)-9-methoxy-4,5,6,11b-tetrahydro-Δ⁴-1,2,4-oxadiazolino<3,2-a>-β-carboline

Base Information

• Chemical Name: 2-(1-cyano-2-phenylvinyl)-5-(ethoxycarbonyl)-9-methoxy-4,5,6,11b-tetrahydro-Δ⁴-1,2,4-oxadiazolino<3,2-a>-β-carboline
• CAS No.: 106544-24-5
• Molecular Formula: C₂₅H₂₂N₄O₄
• Molecular Weight: 442.474

Synonyms:2-(1-cyano-2-phenylvinyl)-5-(ethoxycarbonyl)-9-methoxy-4,5,6,11b-tetrahydro-Δ⁴-1,2,4-oxadiazolino<3,2-a>-β-carboline

Chemical Property of 2-(1-cyano-2-phenylvinyl)-5-(ethoxycarbonyl)-9-methoxy-4,5,6,11b-tetrahydro-Δ⁴-1,2,4-oxadiazolino<3,2-a>-β-carboline

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Technology Process of 2-(1-cyano-2-phenylvinyl)-5-(ethoxycarbonyl)-9-methoxy-4,5,6,11b-tetrahydro-Δ⁴-1,2,4-oxadiazolino<3,2-a>-β-carboline

There total 6 articles about 2-(1-cyano-2-phenylvinyl)-5-(ethoxycarbonyl)-9-methoxy-4,5,6,11b-tetrahydro-Δ⁴-1,2,4-oxadiazolino<3,2-a>-β-carboline 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: 95.0%

Benzylidenemalononitrile (2700-22-3) + 2-oxo-3-(ethoxycarbonyl)-7-methoxy-3,4-dihydro-β-carboline (106544-18-7) → 2-(1-cyano-2-phenylvinyl)-5-(ethoxycarbonyl)-9-methoxy-4,5,6,11b-tetrahydro-Δ4-1,2,4-oxadiazolino<3,2-a>-β-carboline (106544-24-5)

Guidance literature:

In toluene; at 65 ℃; for 7h;

DOI:10.1021/jo00382a014

Reference yield: 95.0%

Benzylidenemalononitrile (2700-22-3) + 2-oxo-3-(ethoxycarbonyl)-7-methoxy-3,4-dihydro-β-carboline (106544-18-7) → (4R,10bR)-2-((E)-1-Cyano-2-phenyl-vinyl)-8-methoxy-4,5,10,10b-tetrahydro-3-oxa-1,3a,10-triaza-cyclopenta[a]fluorene-4-carboxylic acid ethyl ester (106544-24-5)

Guidance literature:

In toluene; at 60 ℃; for 7h;

DOI:10.1016/S0040-4020(01)89838-0

Reference yield:

6-methoxylindole (3189-13-7) → 2-(1-cyano-2-phenylvinyl)-5-(ethoxycarbonyl)-9-methoxy-4,5,6,11b-tetrahydro-Δ4-1,2,4-oxadiazolino<3,2-a>-β-carboline (106544-24-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / Na₂CO₃ / CH₂Cl₂ / 18 h / Ambient temperature

2: 88 percent / HCl, (CH₃)3N*BH₃ / ethanol / 5 h / Ambient temperature

3: 95 percent / CF₃COOH / 1 h / Ambient temperature

4: 95 percent / toluene / 7 h / 65 °C

With hydrogenchloride; trimethylamine-borane; sodium carbonate; trifluoroacetic acid; In ethanol; dichloromethane; toluene;

DOI:10.1021/jo00382a014

upstream raw materials:

Benzylidenemalononitrile

2-oxo-3-(ethoxycarbonyl)-7-methoxy-3,4-dihydro-β-carboline

6-methoxylindole

ethyl 3-bromo-2-(hydroxyimino)propanoate

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