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Synthesis of dihydroquinazolines from 2-aminobenzylamine: N 3 - aryl derivatives with electron-withdrawing groups

Synthesis of dihydroquinazolines from 2-aminobenzylamine: N 3 - aryl derivatives with electron-withdrawing groups

Nadia Gruber, Jimena E Díaz, Liliana R Orelli

Beilstein J Org Chem. 2018 Sep 26;14:2510-2519.

PMID: 30344774

Abstract:

The sequential N-functionalization of 2-aminobenzylamine (2-ABA) followed by cyclodehydration allowed for a straightforward and efficient synthesis of 3,4-dihydroquinazolines with N-aryl substituents bearing electron-withdrawing groups. The sequence involves an initial SNAr displacement, N-acylation and MW-assisted ring closure. Remarkably, the uncatalyzed N-arylation of 2-ABA led to the monosubstitution product using equimolar amounts of both reagents. The individual steps were optimized achieving good to excellent overall yields of the desired heterocycles, avoiding additional protection and deprotection steps. A mechanistic interpretation for the cyclodehydration reaction promoted by trimethylsilyl polyphosphate (PPSE) is also proposed on the basis of literature data and our experimental observations.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP40623469	Trimethylsilyl polyphosphate		40623-46-9	Price

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