Furan-2-carbonyl azide

Base Information

• Chemical Name: Furan-2-carbonyl azide
• CAS No.: 20762-98-5
• Molecular Formula: C₅H₃N₃O₂
• Molecular Weight: 137.098
• DSSTox Substance ID: DTXSID10393834
• Nikkaji Number: J555.780A
• Wikidata: Q82192821
• Mol file: 20762-98-5.mol

Synonyms:furan-2-carbonyl azide;20762-98-5;2-furoyl azide;furoyl azide;DTXSID10393834;AHA100019;AKOS009454612;AKOS015967132;CS-0252451;EN300-60364

Chemical Property of Furan-2-carbonyl azide

Chemical Property:

• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 137.022526347
• Heavy Atom Count: 10
• Complexity: 185

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): 3
• Hazard Codes: 3

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=COC(=C1)C(=O)N=[N+]=[N-]

Technology Process of Furan-2-carbonyl azide

There total 1 articles about Furan-2-carbonyl azide 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:

CH3OC6H4COCH2COC4H3O (133214-18-3) → 4-methoxybenzoyl azide (3532-17-0) + 2-furoyl azide (20762-98-5)

Guidance literature:

With sodium azide; [bis(acetoxy)iodo]benzene; sodium acetate; sodium bromide; In water; acetone; at 50 ℃; for 4h;

DOI:10.1021/acs.joc.8b01417

Reference yield: 93.0%

tert-butylisonitrile (119072-55-8,7188-38-7) + 2-furoyl azide (20762-98-5) + aniline (62-53-3) → N-((tert-butylamino)(phenylamino)methylene)furan-2-carboxamide

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In 1,4-dioxane; at 20 ℃; for 5h; Sealed tube; Inert atmosphere;

DOI:10.1055/s-0036-1588576

Reference yield: 90.0%

Dibenzyl phosphite (17176-77-1) + 2-furoyl azide (20762-98-5) → dibenzyl furan-2-carbonylphosphoramidate

Guidance literature:

With chloro-trimethyl-silane; triethylamine; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1021/acs.orglett.0c03987

upstream raw materials:

CH₃OC₆H₄COCH₂COC₄H₃O

Downstream raw materials:

2-furanyl isocyanate

furan-2-yl carbamic acid ethyl ester

(furan-2-yl)(pyrrolidin-1-yl)methanone

methyl 1,2,3-triazole-4-carboxylate

Refernces

Several convenient methods for the synthesis of 2-amido substituted furans

10.1021/jo026757l

The study presents three novel methods for the synthesis of 2-amido substituted furans, which are valuable intermediates in the synthesis of various natural products and alkaloids. The first method involves the thermolysis of furan-2-carbonyl azide, leading to a Curtius rearrangement and the formation of a furanyl isocyanate intermediate, which is then trapped with different organometallic reagents. The second method is a C-N cross-coupling reaction of bromo-substituted furans with amides, carbamates, and lactams, catalyzed by CuI, yielding 2- and 3-substituted amidofurans in high yields. The third method involves the reaction of cyclic carbinol amides with triflic anhydride to produce R-(trifluoromethyl)sulfonamido-substituted furans under mild conditions. These methods serve to provide diverse and efficient pathways to synthesize 2-amido substituted furans, expanding the synthetic toolkit for the preparation of complex oxygenated polycyclic compounds and potentially facilitating the synthesis of alkaloids.