Synthesis of novel Mannich bases and hybrid Mannich bases related to isoindolin-1,3-dione

Treatment of isoindolin-1,3-dione ( 1 ) with formalin and the appropriate amine or diamine afforded new N-Mannich bases and bis-(Mannich bases) 2 to 6 . The use of the appropriate hydrazide or dihydrazide as the amine component in the Mannich reaction with 1 led to Mannich bases and bis-(Mannich bases) incorporating a hydrazide moiety. The synthetic potential of sec-Mannich bases as precursors in synthesis of hybrid Mannich bases incorporating 1 was described. The N-alkylation of 1 with ketonic Mannich bases was investigated.     

Mannich bases derived from p-diethynylbenzene

Conclusions By the Mannich reaction with diacetylenic alcohols derived from p-diethynylbenzene a number of di~ acetylenic amino alcohols were prepared, and these were hydrogenated to the corresponding saturated compounds.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 397–404, February, 1967.     

Interaction of Mannich bases with triethyl phosphite

Conclusions A study of the kinetics of the reaction of aliphatic ketone Mannich bases with acetic acid indicated that this reaction is a reaction of elimination of vinyl ketone from a salt of the base with the acid and is a first-order reaction.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 825–828, April, 1969.     

Phenylhydrazines. Structure and basicity

The main properties of phenylhydrazines are governed by the p-character of the unshared electron pair of the nitrogen of imino group changing in keeping with sp ³ → sp ²-regibridization of its atomic orbitals under the steric and electronic (-I effect of amino group) effect of substituents.     

Vicinal N,C-difluorination of secondary polynitroalkylamine Mannich bases

The direct fluorination of Mannich bases containing nitro groups in one or two alkyl substituants in the position relative to the amine nitrogen gives previously unreported vicinal N,C-difluorides.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1692–1693, July, 1991.     

Novel acetal-containing calix[4]resorcinolarene-based Mannich bases

The reaction of calix[4]resorcinolarene with methylaminoacetaldehyde dimethyl acetal and formalin gave novel acetal-containing calix[4]resorcinolarene derivatives aminomethylated at the upper rim.     

Synthesis and characterization of Mannich bases of lawsone and their anticancer activity

Abstract

Natural and synthetic naphthoquinones are known for a large number of biological activities. Lawsone (2-hydroxy-1, 4-naphthoquinone) is a simplest naturally occurring compound obtained from dried henna (Lawsonia inermis) leaves. In literature, some lawsone derivatives have been reported to exhibit anticancer activity. Hence, a clean and facile one-pot protocol was developed for the synthesis of new aminonaphthoquinones derived from lawsone by three-component Mannich reaction, at room temperature for potential anti-cancer application. Herein we present a small library of Mannich bases with different amines and aromatic aldehydes with moderate to high yield. Synthesized compounds were characterized using various spectroscopic techniques. The anticancer activity (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay) along with nuclear morphology assessment (4′,6-diamidino-2-phenylindole or DAPI staining), apoptosis assessment (acridine orange/ ethidium bromide staining), hemolysis and DNA ladder assay evaluated on human liver carcinoma cell line HepG2 are presented.     

Facile synthesis of aminonaphthoquinone Mannich bases by noncatalytic multicomponent reaction

Mannich bases are formed in a noncatalytic multicomponent reaction, which is promoted by ultrasound irradiation. The procedure avoids the use of toxic solvents, catalyst, and purification, generating the desired compounds in excellent yields and short reaction times.     

Structure and nitrogen basicity of pyridine metal extractants

The effect of various substituents in pyridine derivatives upon the basicity of the nitrogen was discussed. The dissociation constants were correlated with the Hammett parameters and compared with copper extraction data. The analysis of nitrogen basicity in pyridine derivatives permits to select possible structures of extractants for metal extraction from chloride solutions.     

Photo- and thermochromic mannich bases. 1. Mannich bases from 3,5-di-tert-butyl-4-hydroxybenzaldehyde and 2-naphthols

Mannich bases exhibiting photo- and thermochromic properties in solutions were synthesized from 3,5-di-tert-butyl-4-hydroxybenzaldehyde and 2-naphthols. An investigation of an acetyl derivative of methylenequinone, modeling a product of photo- and thermochromic transformations, proved that the color change of solutions of the Mannich bases is due to reversible dissociation into colored methylenequinones and morpholine. On the basis of data of x-ray diffraction analysis of one of the Mannich bases, characteristics of their molecular structure were determined, and reasons were stated for their effect on the dissociation mechanism.