1,2,3,3a-Tetraaza-3aH-indene

Base Information

• Chemical Name: 1,2,3,3a-Tetraaza-3aH-indene
• CAS No.: 274-87-3
• Molecular Formula: C5H4 N4
• Molecular Weight: 120.114
• Hs Code.: 2933990090
• Mol file: 274-87-3.mol

Synonyms:1,2,3-Triazaindolizine;NSC 109852; NSC 838; Pyridotetrazole

Chemical Property of 1,2,3,3a-Tetraaza-3aH-indene

Chemical Property:

• Melting Point: 156-157 °C(Solv: ethyl acetate (141-78-6))
• PKA: 0.80±0.30(Predicted)
• PSA: 43.08000
• Density: 1.48g/cm³
• LogP: 0.12430
• Storage Temp.: Inert atmosphere,Room Temperature

Purity/Quality:

97% ^*data from raw suppliers

Tetrazolo[1,5-A]Pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,2,3,3a-Tetraaza-3aH-indene

There total 6 articles about 1,2,3,3a-Tetraaza-3aH-indene 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: 83.0%

pyridine (110-86-1) + p-nitrophenyl isocyanide (1984-23-2) → 2-[1-(4-nitro-phenyl)-1H-tetrazol-5-yl]-pyridine + tetrazolo[1,5-a]pyridine (274-87-3) + pyridine-2-carboxylic acid (4-nitro-phenyl)amide (61349-99-3)

Guidance literature:

pyridine; With fluorine; In chloroform; at -78 - -60 ℃;

p-nitrophenyl isocyanide; With trimethylsilylazide; In chloroform; at -50 - 0 ℃;

DOI:10.1016/j.tetlet.2005.05.066

Reference yield: 81.0%

pyridine (110-86-1) + 1-isocyano-4-(trifluoromethyl)benzene (139032-23-8) → N-(4-trifluorophenyl)-2-pyridinecarboxamide + 2-[1-(4-trifluoromethyl-phenyl)-1H-tetrazol-5-yl]-pyridine + tetrazolo[1,5-a]pyridine (274-87-3)

Guidance literature:

pyridine; With fluorine; In chloroform; at -78 - -60 ℃;

1-isocyano-4-(trifluoromethyl)benzene; With trimethylsilylazide; In chloroform; at -50 - 0 ℃;

DOI:10.1016/j.tetlet.2005.05.066

Reference yield: 75.0%

pyridine (110-86-1) + phenyl isocyanate (1197040-29-1,931-54-4) → tetrazolo[1,5-a]pyridine (274-87-3) + N-phenylpicolinamide (10354-53-7) + 2-(1-phenyl-1H-tetrazol-5-yl)-pyridine

Guidance literature:

pyridine; With fluorine; In chloroform; at -78 - -60 ℃;

phenyl isocyanate; With trimethylsilylazide; In chloroform; at -50 - 0 ℃;

DOI:10.1016/j.tetlet.2005.05.066

upstream raw materials:

pyridine N-oxide

trimethylsilylazide

methanesulfonyl chloride

pyridine

Downstream raw materials:

Tetramethylenetetrazole

3-dimethylamino-2H-2,4-diazabicyclo[3.2.0]hepta-3,6-diene

C₁₃H₁₄N₄

2-(4-benzyl-1H-1,2,3-triazol-1-yl)pyridine

Refernces

Fused tetrazoles as azide surrogates in click reaction: Efficient synthesis of N-heterocycle-substituted 1,2,3-triazoles

10.1021/ol100745d

The research investigates the use of various pyrido-, quinolino-, pyrazino-, and quinoxalinotetrazoles as azide surrogates in Cu-catalyzed click reactions with alkynes to efficiently synthesize N-heterocyclic derivatives of 1,2,3-triazoles. The study aims to develop an efficient method for synthesizing these biologically important 1,2,3-triazoles, which have a wide range of applications, including controlling arthropod pests, treating substance-related disorders, and exhibiting antibacterial and antimicrobacterial activity. The researchers optimized the reaction conditions, finding that using (CuOTf)2·C6H6 as the catalyst in toluene or THF at room temperature or elevated temperatures yielded good to excellent results. They tested the generality of these conditions with different tetrazoles and alkynes, achieving high yields of the desired triazoles. However, they found that pyridotetrazoles could not be used as azide precursors in Ru-catalyzed synthesis of 1,5-disubstituted triazoles, likely due to deactivation of the Ru-catalyst by chelation with the nitrogen atom of the pyridine ring.