125659-45-2

Basic information

• Product Name: 2-Pyrrolidinone, 1-(2-azidobenzoyl)-
• CAS NO: 125659-45-2
• Molecular Formula: C11H10N4O2
• Molecular Weight: 230.226
• Mol File: 125659-45-2.mol

Chemical Properties

• CAS DataBase Reference: 2-Pyrrolidinone, 1-(2-azidobenzoyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyrrolidinone, 1-(2-azidobenzoyl)-(125659-45-2)
• EPA Substance Registry System: 2-Pyrrolidinone, 1-(2-azidobenzoyl)-(125659-45-2)

Safety Data

• Hazardous Substances Data: 125659-45-2(Hazardous Substances Data)

Upstream product

• 616-45-5 2-pyrrolidinon 
• 31162-13-7 2-azidobenzoic acid 
• 34897-85-3 o-azidobenzoyl chloride 

Downstream Products

• 486-64-6 (S)-3-hydroxy-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one 
• 530-53-0 deoxyvasicinone 

Relevant articles and documents

A polymer-assisted solution-phase strategy for the synthesis of fused [2,1-b]quinazolinones and the preparation of optically active vasicinone

An efficient preparation of fused [2,1-b]quinazolinones has been developed utilizing polymer-supported reagents. (±)- Vasicinone was converted into its dione by oxidation with poly (4-vinylpyridiniumdichromate). An efficient method has been developed for the synthesis of (d)- and (l)-vasicinone via asymmetric reduction of pyrrolo[2,1-b]quinazoline-3,9-dione by employing NaBH4/Me3SiCl as the reducing agent and polymer-supported chiral sulfonamide as catalyst. Georg Thieme Verlag Stuttgart.

Efficient solid-phase synthesis of highly functionalized 1,4-benzodiazepin-5-one derivatives and related compounds by intramolecular aza-wittig reactions

Due to their widespread biological activities and favorable pharmacokinetic properties, benzodiazepines were among the first classes of small molecules to be synthesized on solid supports. Since then, there have been numerous reports on the synthesis of similar skeletons. We have employed the T1 triazene linker to yield 1,4-benzodiazepin-5-one. Starting from various substituted triazene resins, cleavage in the presence of an azide donor, such as trimethylsilylazide, gave rise to aryl azides. Intramolecular aza-Wittig reactions produced the appropriately functionalized N-heterocycles. By using this route, the natural product deoxyvasicinone and related compounds were prepared.

One pot conversion of azido arenes to N-arylacetamides and N-arylformamides: Synthesis of 1,4-benzodiazepine-2,5-diones and fused [2,1-b]quinazolinones

Sodium iodide in acidic media has been employed for the synthesis of N-arylformamides and N-arylacetamides. The NaI/acetic acid reagent system has also been extended for the synthesis of 1,4-benzodiazepine-2,5-diones, pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones, and fused [2,1-b]quinazolinones.

Chemoenzymatic synthesis of pyrrolo[2,1-b]quinazolinones: Lipase-catalyzed resolution of vasicinone

A facile synthesis of bronchodilatory pyrrolo[2,1-b]quinazoline alkaloids by azidoreductive cyclization strategy employing TMSCl-NaI and bakers' yeast is described. Both the chemical and enzymatic methods are mild and take place at room temperature in good yields. Further, synthesis and resolution of vasicinone has been carried out by employing different lipases. It has been observed that lipase PS provides acetate of (S)-vasicinone in 98% ee.

A NEW EFFICIENT SYNTHESIS OF IMIDAZOLINONES AND QUINAZOLINONE BY INTRAMOLECULAR AZA-WITTIG REACTION

A new synthesis of imidazolinones and quinazolinones by intramolecular aza-Wittig reaction is described.Readily available azido substituted imides 4, 6, 10, and 12 reacted with triphenylphosphine or tributylphosphine to afford the corresponding imidazolin