5H-IMIDAZO[2,1-B][1,3]OXAZINE, 6-AZIDO-6,7-DIHYDRO-2-NITRO-, (6S)-

Base Information

• Chemical Name: 5H-IMIDAZO[2,1-B][1,3]OXAZINE, 6-AZIDO-6,7-DIHYDRO-2-NITRO-, (6S)-
• CAS No.: 187235-64-9
• Molecular Formula: C₆H₆N₆O₃
• Molecular Weight: 210.152
• Mol file: 187235-64-9.mol

Synonyms:5H-Imidazo[2,1-b][1,3]oxazine,6-azido-6,7-dihydro-2-nitro-, (S)-

Chemical Property of 5H-IMIDAZO[2,1-B][1,3]OXAZINE, 6-AZIDO-6,7-DIHYDRO-2-NITRO-, (6S)-

Chemical Property:

• Melting Point: 152.0-152.4 °C
• PSA: 122.62000
• LogP: 0.83856

Purity/Quality:

98%Min ^*data from raw suppliers

(6S)-6-AZIDO-6,7-DIHYDRO-2-NITRO-5H-IMIDAZO-[2,1-B][1,3]-OXAZINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5H-IMIDAZO[2,1-B][1,3]OXAZINE, 6-AZIDO-6,7-DIHYDRO-2-NITRO-, (6S)-

There total 5 articles about 5H-IMIDAZO[2,1-B][1,3]OXAZINE, 6-AZIDO-6,7-DIHYDRO-2-NITRO-, (6S)- 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: 67.0%

(6R)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol (187235-13-8) → (S)-6-azido-6,7-dihydro-2-nitro-5H-imidazo[2,1-b][1,3]oxazine (187235-64-9)

Guidance literature:

With di-tert-butyl-diazodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/jm801374t

Reference yield: 46.0%

(R)-6,7-dihydro-2-nitro-5H-imidazo[2,1-b][1,3]oxazin-6-yl methanesulfonate (1129693-19-1) → (S)-6-azido-6,7-dihydro-2-nitro-5H-imidazo[2,1-b][1,3]oxazine (187235-64-9)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 70 ℃; for 48h; Inert atmosphere;

DOI:10.1021/jm801374t

Reference yield:

C10H14N4O7 → (S)-6-azido-6,7-dihydro-2-nitro-5H-imidazo[2,1-b][1,3]oxazine (187235-64-9)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridinium p-toluenesulfonate / dichloromethane / 20 °C

2: caesium carbonate / methanol / 0 °C

3: hydrogenchloride / methanol; ethanol; water / 1 h / 20 °C

4: 15 h / 20 °C

5: sodium azide / N,N-dimethyl-formamide / 15 h / 70 °C

With hydrogenchloride; sodium azide; pyridinium p-toluenesulfonate; caesium carbonate; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

(6R)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol

(R)-6,7-dihydro-2-nitro-5H-imidazo[2,1-b][1,3]oxazin-6-yl methanesulfonate

(3R)-tetrahydropyranyloxy-6-nitro-2H-3,4-dihydro[2,1-b]imidazopyran

Refernces

• 1、 Kim, Pilho,Kang, Sunhee,Boshoff, Helena I.,Jiricek, Jan,Collins, Margaret,Singh, Ramandeep,Manjunatha, Ujjini H.,Niyomrattanakit, Pornwaratt,Zhang, Liang,Goodwin, Michael,Dick, Thomas,Keller, Thomas H.,Dowd, Cynthia S.,Barry III, Clifton E.. "Structure-activity relationships of antitubercular nitroimidazoles. 2. determinants of aerobic activity and quantitative structure-activity relationships". experimental part. p. 1329 - 1344. Retrieved 2009/12/07.