1H-3,7,8-tris(4-methoxyphenyl)pyrrolo<2,1-c><1,4>-oxazin-1-one

Base Information

• Chemical Name: 1H-3,7,8-tris(4-methoxyphenyl)pyrrolo<2,1-c><1,4>-oxazin-1-one
• CAS No.: 170238-97-8
• Molecular Formula: C₂₈H₂₃NO₅
• Molecular Weight: 453.494
• Mol file: 170238-97-8.mol

Synonyms:1H-3,7,8-tris(4-methoxyphenyl)pyrrolo<2,1-c><1,4>-oxazin-1-one

Chemical Property of 1H-3,7,8-tris(4-methoxyphenyl)pyrrolo<2,1-c><1,4>-oxazin-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1H-3,7,8-tris(4-methoxyphenyl)pyrrolo<2,1-c><1,4>-oxazin-1-one

There total 25 articles about 1H-3,7,8-tris(4-methoxyphenyl)pyrrolo<2,1-c><1,4>-oxazin-1-one 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: 60.0%

methyl 3,4-bis(4-methoxyphenyl)-1-[2-(4-methoxyphenyl)-2-oxoethyl]-1H-pyrrole-2-carboxylate (170238-96-7) → 1H-3,7,8-tris(4-methoxyphenyl)pyrrolo<2,1-c><1,4>-oxazin-1-one (170238-97-8)

Guidance literature:

methyl 3,4-bis(4-methoxyphenyl)-1-[2-(4-methoxyphenyl)-2-oxoethyl]-1H-pyrrole-2-carboxylate; With potassium tert-butylate; In diethyl ether; water; at 0 - 20 ℃;

With sodium acetate; In acetic anhydride; at 100 ℃; for 2.5h; Further stages.;

DOI:10.1021/jo9915224

Reference yield:

(E)-1,3-bis(4-methoxyphenyl)-2-propene-1-one (41564-67-4) → 1H-3,7,8-tris(4-methoxyphenyl)pyrrolo<2,1-c><1,4>-oxazin-1-one (170238-97-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 98 percent / H₂O₂, NaOH / ethanol; H₂O / 6.5 h / Ambient temperature

2: 1.) BF₃*Et₂O, 2.) NH₂OH*HCl, pyridine / 1.) Et₂O, reflux, 45 min, 2.) EtOH, reflux, 20 h

3: 94 percent / H₂ / Pd on charcoal / tetrahydrofuran / 19 h / 760 Torr / Ambient temperature

4: pyridine / tetrahydrofuran

5: 52 percent / TiCl₃, C₈K / 1,2-dimethoxy-ethane / 1.5 h / Heating

6: 91 percent / K₂CO₃ / acetone / 21 h / Heating

7: 1.) t-BuOK, H₂O, 2.) Ac₂O, NaOAc / 1.) Et₂O, room temperature, 45 min, 2.) 100 deg C, 2.5 h

With pyridine; sodium hydroxide; titanium(III) chloride; boron trifluoride diethyl etherate; hydroxylamine hydrochloride; potassium tert-butylate; water; hydrogen; dihydrogen peroxide; sodium acetate; acetic anhydride; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; water; acetone;

DOI:10.1021/jo00125a068

Reference yield:

[3-(4-methoxyphenyl)oxiran-2-yl]-(4-methoxyphenyl)methanone (55097-58-0) → 1H-3,7,8-tris(4-methoxyphenyl)pyrrolo<2,1-c><1,4>-oxazin-1-one (170238-97-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) BF₃*Et₂O, 2.) NH₂OH*HCl, pyridine / 1.) Et₂O, reflux, 45 min, 2.) EtOH, reflux, 20 h

2: 94 percent / H₂ / Pd on charcoal / tetrahydrofuran / 19 h / 760 Torr / Ambient temperature

3: pyridine / tetrahydrofuran

4: 52 percent / TiCl₃, C₈K / 1,2-dimethoxy-ethane / 1.5 h / Heating

5: 91 percent / K₂CO₃ / acetone / 21 h / Heating

6: 1.) t-BuOK, H₂O, 2.) Ac₂O, NaOAc / 1.) Et₂O, room temperature, 45 min, 2.) 100 deg C, 2.5 h

With pyridine; titanium(III) chloride; boron trifluoride diethyl etherate; hydroxylamine hydrochloride; potassium tert-butylate; water; hydrogen; sodium acetate; acetic anhydride; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; acetone;

DOI:10.1021/jo00125a068

upstream raw materials:

methyl 3,4-bis(4-methoxyphenyl)-1-[2-(4-methoxyphenyl)-2-oxoethyl]-1H-pyrrole-2-carboxylate

1-[2-hydroxy-2-(4-methoxyphenyl)ethyl]-3,4-bis(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxylic acid

3,7,8-tris(4-methoxyphenyl)-1-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carboxylic acid

3,7,8-tris(4-methoxyphenyl)-1-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carboxylic acid 2-(trimethylsilyl)ethyl ester

Downstream raw materials:

3,7,8-tris(4-hydroxyphenyl)-1H-pyrrolo[2,1-c][1,4]oxazin-1-one

Refernces

• 1、 Hinze, Claudia,Kreipl, Andreas,Terpin, Andreas,Steglich, Wolfgang. "Synthesis of simple 3,4-diarylpyrrole-2,5-dicarboxylic acids and lukianol A by oxidative condensation of 3-arylpyruvic acids with ammonia". . p. 608 - 612. Retrieved 2008/01/04.
• 2、 Liu, Jian-Hui,Yang, Qing-Chuan,Mak, Thomas C. W.,Wong, Henry N. C.. "Highly regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles: A formal total synthesis of lukianol A". . p. 3587 - 3595. Retrieved 2007/10/03.