Synthesis of isatin‐N‐mannich bases

Abstract

The synthesis of a series of isatin-N-Mannich bases derived from isatin, 5-methyl and 5-bromoisatins a s the active hydrogen component and dimethylamine, diethylamine, morpholine, piperidine, N-ethylcyclohexylamine, 3-azabicyclo[3.2.2]nonane and 3-azabicyclo[3.2. lloctane a s the secondary amine moiety is described. These compounds a r e to be screened for their pharmacological properties.

Trityl Isothiocyanate Support for Solid-Phase Synthesis

“…The next step involves conversion of the supported isatin thiosemicarbazones 4 to the N-dialkylaminomethyl isatin derivatives 5. Treatment of 4a with excess piperidine and aqueous formaldehyde in DMF (method A, Scheme 2) following a modification of the literature procedure 8 gives the supported isatin derivative 5a. This procedure could also be employed for the preparation of 5b, 5c, and 5e (prepared from dimethylamine and formaldehyde), but not for 5d.…”

1-(Morpholinomethyl)indoline-2,3-dione

“…The title compound was synthesized according the literature method (Varma & Nobles, 1966). Isatin (1 mmol), formaldehyde (1.2 mmol) and morpholin (1.2 mmol) were dissolved in methanol (20 ml).…”

“…For the synthesis of isatin-N-Mannich bases, see: Varma & Nobles ((1966). For the bioactivity of isatin derivatives, see: Glover et al (1980Glover et al ( , 1988; Maysinger et al (1980).…”

Synthesis of a New Series of N‐Mannich Bases and Polyhydroxy Mannich Bases of Pharmaceutical Interest Related to Isatin and Its Schiff Bases

“…The N‐ Mannich bases derived from NH ‐heterocycles and their derivatives have received significant attention due to their wide range of biological and pharmacological activities . In particular, much interest has centered around N‐ Mannich bases of isatin, and related compounds, which possess a broad spectrum of action including antibacterial , anticonvulsant , anti‐HIV , antifungal , cytotoxic, and anticancer activities.…”