ChemInform Abstract: 6,11‐Dihydro‐5H‐pyrimidino(4,5‐a)carbazoles.

Gazengel, Jean-Marie; Lancelot, J.-C.; Rault, Syl­vain; Robba, M.

doi:10.1002/chin.199118188

Cited by 3 publications

(5 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Further evidence is that the reaction of 2-aminobenzamide with DMF under the standard conditions only afforded quinazolinone, and no product was detected by the reaction of 1a with DMF in hydrochloride solution. In addition, this proposed mechanism was also confirmed by the literature, , and quinazolinones were provided by the cyclization of o -amidobenzamides …”

supporting

confidence: 74%

A New and Facile Synthesis of Quinazoline-2,4(1H,3H)-diones

Chen

Shi

et al. 2009

Org. Lett.

View full text Add to dashboard Cite

show abstract

supporting

confidence: 74%

A New and Facile Synthesis of Quinazoline-2,4(1H,3H)-diones

Chen

Shi

et al. 2009

Org. Lett.

View full text Add to dashboard Cite

show abstract

“…Preparation of the pyrimidone ring was accomplished using a slightly modified literature procedure . Chloride 9 (Scheme ) was first suspended in formic acid (42 equiv) and heated to provide a solution.…”

Section: Discussion and Resultsmentioning

confidence: 99%

“…Preparation of the pyrimidone ring was accomplished using a slightly modified literature procedure. 10 Chloride 9 (Scheme 5) was first suspended in formic acid (42 equiv) and heated to provide a solution. Addition of 9 N sulfuric acid promoted the nitrile hydrolysis, formamide condensation, and subsequent cyclization to give product 10.…”

Section: Discussion and Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Process Research and Kilogram Synthesis of an Investigational, Potent MEK Inhibitor

Zhao

Zhu

Provencal

et al. 2012

Org. Process Res. Dev.

View full text Add to dashboard Cite

Process research of 1 was conducted, and an efficient, scalable route was developed. The key intermediate, a multisubstituted fluoropyridone, was formed in one pot via a three-step cascade reaction: condensation between α-fluoromalonate and malononitrile, methyl amide formation, and intramolecular cyclization. Chlorination of the hydroxyl functionality and cyclization with formic acid provided the desired pyridopyrimidone core in high yield. Subsequent N-alkylation with the nosylate of (R)glycerol acetonide and displacement of the chlorine with 2-fluoro-4-iodoaniline proceeded successfully with good yields. Final acid-catalyzed deprotection of the acetonide functionality followed by a controlled crystallization protocol afforded the active pharmaceutical ingredient (API) with the desired polymorph. Compared to the initial synthesis, this route was more concise (six steps compared to the original nine steps), and the overall yield was improved significantly (from 3% to 25%). These improvements allowed for production of multikilograms of 1.

show abstract

“…However, this is the most probable mechanism as per the literature. 35,56 Substrate Study. Quinazoline-2,4(1H,3H)-dione.…”

Section: Organic Process Research and Developmentmentioning

confidence: 99%

Carbon Dioxide Mediated Novel Synthesis of Quinazoline-2,4(1H,3H)-dione in Water

Rasal

Yadav

2016

Org. Process Res. Dev.

View full text Add to dashboard Cite

A novel, efficient, and scalable CO2 mediated synthesis of quinazoline-2,4(1H,3H)-dione was developed by a simple cyclization of 2-aminobenzonitrile with DMF in water as the solvent. This is the first report of its kind. DMF was used as the necessary carbon source in the synthesis of quinazoline-2,4(1H,3H)-dione. This synthetic protocol is very efficient; it gives >99% conversion with excellent selectivity. The product was isolated by filtration because of the highly insoluble nature of quinazoline-2,4(1H,3H)-dione in water. The co-product, dimethyl amine, also has industrial importance, and the CO2 that is used can be recycled. This protocol has wide-spread applications in the syntheses of benzimidazole and benzothiazole.

show abstract

ChemInform Abstract: 6,11‐Dihydro‐5H‐pyrimidino(4,5‐a)carbazoles.

Cited by 3 publications

References 1 publication

A New and Facile Synthesis of Quinazoline-2,4(1H,3H)-diones

A New and Facile Synthesis of Quinazoline-2,4(1H,3H)-diones

Process Research and Kilogram Synthesis of an Investigational, Potent MEK Inhibitor

Carbon Dioxide Mediated Novel Synthesis of Quinazoline-2,4(1H,3H)-dione in Water

Contact Info

Product

Resources

About