1-tosyl-4-vinyl-1,4-dihydro-2H-benzo[d] [1,3]oxazin-2-one

Base Information

• Chemical Name: 1-tosyl-4-vinyl-1,4-dihydro-2H-benzo[d] [1,3]oxazin-2-one
• CAS No.: 1038502-72-5
• Molecular Formula: C₁₇H₁₅NO₄S
• Molecular Weight: 329.376
• Mol file: 1038502-72-5.mol

Synonyms:1-tosyl-4-vinyl-1,4-dihydro-2H-benzo[d] [1,3]oxazin-2-one

Chemical Property of 1-tosyl-4-vinyl-1,4-dihydro-2H-benzo[d] [1,3]oxazin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-tosyl-4-vinyl-1,4-dihydro-2H-benzo[d] [1,3]oxazin-2-one

There total 10 articles about 1-tosyl-4-vinyl-1,4-dihydro-2H-benzo[d] [1,3]oxazin-2-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:

3-(2-oxopropyl)-4-vinyl-3,4-dihydroquinolin-2(1H)-one (899438-69-8) + p-toluenesulfonyl chloride (98-59-9) → 1-tosyl-4-vinyl-1,4-dihydro-2H-benzo[d] [1,3]oxazin-2-one (1038502-72-5)

Guidance literature:

3-(2-oxopropyl)-4-vinyl-3,4-dihydroquinolin-2(1H)-one; With sodium hydride; triethylamine; In tetrahydrofuran; for 1h; Inert atmosphere;

p-toluenesulfonyl chloride; In tetrahydrofuran; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1021/jacs.6b04364

Reference yield:

2-Aminobenzyl alcohol (5344-90-1) → 1-tosyl-4-vinyl-1,4-dihydro-2H-benzo[d] [1,3]oxazin-2-one (1038502-72-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydrogencarbonate / 1,4-dioxane; water / 2 h / 0 - 20 °C / Inert atmosphere

2.1: manganese(IV) oxide / dichloromethane / 4 h / 20 °C / Inert atmosphere

3.1: tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

3.2: 2 h / 20 °C / Inert atmosphere

4.1: sodium hydride; triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

4.2: 4 h / Inert atmosphere

With manganese(IV) oxide; sodium hydride; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;

DOI:10.1021/acs.orglett.8b00905

Reference yield:

anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) → 1-tosyl-4-vinyl-1,4-dihydro-2H-benzo[d] [1,3]oxazin-2-one (1038502-72-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

2.1: sodium hydrogencarbonate / 1,4-dioxane; water / 2 h / 0 - 20 °C / Inert atmosphere

3.1: manganese(IV) oxide / dichloromethane / 4 h / 20 °C / Inert atmosphere

4.1: tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

4.2: 2 h / 20 °C / Inert atmosphere

5.1: sodium hydride; triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

5.2: 4 h / Inert atmosphere

With manganese(IV) oxide; lithium aluminium tetrahydride; sodium hydride; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;

DOI:10.1021/acs.orglett.8b00905

upstream raw materials:

3-(2-oxopropyl)-4-vinyl-3,4-dihydroquinolin-2(1H)-one

p-toluenesulfonyl chloride

2-(methyloxycarbonyl)aminobenzaldehyde

methyl ortho-(hydroxymethyl)phenyl carbamate

Refernces

• 1、 Chen, Xiangyang,Hao, Jiping,Houk, K. N.,Li, Yingzi,Lou, Liguang,Quan, Haitian,Song, Bichao,Wang, Lu,Xia, Yuanzhi,Xie, Peipei,Xu, Zhongliang,Yang, Weibo. "Pd-Catalyzed Decarboxylative Olefination: Stereoselective Synthesis of Polysubstituted Butadienes and Macrocyclic P-glycoprotein Inhibitors". supporting information. p. 9982 - 9992. Retrieved 2020/06/27.
• 2、 Guo, Chang,Fleige, Mirco,Janssen-Müller, Daniel,Daniliuc, Constantin G.,Glorius, Frank. "Cooperative N-Heterocyclic Carbene/Palladium-Catalyzed Enantioselective Umpolung Annulations". supporting information. p. 7840 - 7843. Retrieved 2016/07/07.