Mannich Reaction as a Key Strategy for the Synthesis of Benzoazacrown Ethers and Benzocryptands

Victor N. Pastushok; Jerald S. Bradshaw; Andrei V. Bordunov; Reed M. Izatt

doi:10.1021/jo9607931

Mannich Reaction as a Key Strategy for the Synthesis of Benzoazacrown Ethers and Benzocryptands

J Org Chem. 1996 Oct 4;61(20):6888-6892. doi: 10.1021/jo9607931.

Authors

Victor N. Pastushok¹, Jerald S. Bradshaw, Andrei V. Bordunov, Reed M. Izatt

Affiliation

¹ Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, and IBC Advanced Technologies, Inc., P.O. Box 98, American Fork, Utah 84003.

PMID: 11667583
DOI: 10.1021/jo9607931

Abstract

A convenient method for the synthesis of mono- and polycyclic azacrown macrocycles containing aromatic fragments using the Mannich condensation of phenols and secondary diamines has been studied. This new approach allowed the synthesis of bisphenols connected by oligoazaoxaalkane units in good yields without the need to protect the phenolic OH groups. These bisphenols (13-16) were alkylated with ditosylates of polyethylene glycols to give benzoazacrown ethers 25-30. Intermediate bisphenols 13-15 were also treated with three bis(methoxymethyl)-substituted diamines to form benzoazacrowns 10-12 containing internal phenolic functions. Phenol-containing mono- (11) and bicyclic (3, n = 1) compounds, which were synthesized via the Mannich aminomethylation process, were used as building blocks for construction of bi- (32) and tricyclic (33) ligands.