A direct access to bioactive fused N-heterocyclic acetic acid derivatives

Abstract

A Cu-catalyzed new sequence involving the Ullmann type intermolecular C-C followed by an intramolecular C-N coupling and then intramolecular aza-Michael type addition (and oxidation) in a single pot afforded various fused N-heterocyclic acetic acid derivatives as inhibitors of PDE4.

4-Azidocinnoline—Cinnoline-4-amine Pair as a New Fluorogenic and Fluorochromic Environment-Sensitive Probe

“…Chemicals were used without further purification. 4-Chloro-2-iodoaniline [49] and ethynytltriazene 1a [35,50] were synthesized by known procedures without any modifications. Evaporation of solvents and concentration of reaction mixtures were performed in vacuum at 35 • C on a rotary evaporator.…”

Recent applications of aminouracil in multicomponent reactions

“…Synthesis of pyrazolo-pyrimido [4,5-d]pyrimidine derivatives in an ionic liquid. 78 Shiri and co-workers efficiently carried out a new intramolecular cyclization method via the one-pot reaction 2-chloroquinoline-3-carbaldehydes (48) 80 The nanocatalyst gave the target products high yields (85-98%) during short reaction times (5-10 min). In continuation, the authors investigated the reaction of N,N'-disubstituted-6-aminouracil (2), isothiocyanate (51) with a variety of aldehydes (1) under the optimized conditions.…”

“…This method proved to be of considerable utility to researchers to obtain desired complex heterocyclic frameworks by condensation of more than two reactants in a single operational step. [41][42][43][44][45][46][47][48] Herein, in continuation of studies towards the synthesis of heterocyclic scaffolds via multicomponent reactions, [49][50][51][52] and because the 6-aminouracil is frequently used as a starting material in synthesizing these compounds. This review is devoted to recent applications of 6-aminouracil and its derivatives in synthesizing diverse heterocyclic compounds based on MCRs from 2015 to 2020.…”

One-Pot Access to Benzo[a]carbazoles via Palladium(II)-Catalyzed Hetero- and Carboannulations

“…The ortho -ethynyl­aniline derivatives S1 were prepared in three steps starting from aniline derivatives (see Scheme S1 in the Supporting Information) using known methods. , Initially, iodination of the aniline derivatives using I 2 and sodium bicarbonate in toluene–water (3:7) afforded 2-iodoaniline derivatives; coupling of this product with TMS-acetylene under “ Sonogashira reaction ” conditions, followed by desilylation of the resulting product, led to the desired ortho -ethynyl­aniline derivatives S1 reported previously . Product S1 underwent coupling with commercially available ortho -iodophenylacetonitrile derivatives in a subsequent step employing “ Sonogashira reaction ” conditions to afford amino-alkyne S2 tethered with a nitrile group (see Scheme S2 in the Supporting Information).…”