Herein, a one-pot protocol to synthesize tetracyclic triazole-piperazine-quinazolinone-fused N-heterocyclic scaffolds is reported. In this strategy, a tandem approach of two highly efficient synthetic reactions, click and cross-dehydrogentive coupling reactions, with high atom economy were employed to obtain the target N-fused scaffolds. Being highly functional group tolerable, this method has broad substrate scope. Interestingly, some of these derivatives showed strong white solid-state fluorescence.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.orglett.1c03435DOI Listing

Publication Analysis

Top Keywords

synthesis n-fused
4
n-fused triazole-piperazine-quinazolinones
4
triazole-piperazine-quinazolinones one-pot
4
one-pot tandem
4
tandem click
4
click reaction
4
reaction cross-dehydrogenative
4
cross-dehydrogenative coupling
4
coupling one-pot
4
one-pot protocol
4

Similar Publications

A cascade transformation of C2-quaternary indoxyls leading to an efficient assembly of complex (dihydro)indolo[1,2-]quinolin-5-one ring systems is reported. The method involves the gram-scale preparation of 2-(2-aryl-3-oxoindolin-2-yl)-2-phenylacetonitriles which are then converted with methyl ketones to the corresponding 2-(2-oxo-2-aryl(alkyl)ethyl)-2-phenylindolin-3-ones. The latter can either be isolated with good yields (75-96%) or, in the case of -nitroacetophenone, used for further base-assisted intramolecular SAr cyclization resulting in indoxyl-fused quinolone-4 hybrids (up to 95%).

View Article and Find Full Text PDF

Two different types of novel nonaromatic acenaphthene fused macrocycles such as acenaphthene fused dithiaporphyrin(3.1.1.

View Article and Find Full Text PDF

The development of chemical scaffolds that target highly conserved RNA received attention due to its significance in splicing, nuclear organization, and gene expression in disease progression pathways. Here, we synthesized a series of N-fused quinazolino-quinazoline-diones a PIDA-induced C-N coupling methodology to target . Interestingly, compound 2z binds to the UUG pocket of a RNA triple-helix through intercalation, evidenced from molecular docking studies, fluorescence-based assay and CD experiments.

View Article and Find Full Text PDF

A highly enantioselective Ir-catalyzed asymmetric hydrogenation of 2,5-disubstituted pyrrolo[1,2-][1,2,4]triazolo[5,1-]pyrazines containing four nitrogen atoms has been first realized. Under additive-free conditions, a variety of chiral 2,5-disubstituted 5,6-dihydropyrrolo[1,2-][1,2,4]triazolo[5,1-]pyrazines can be afforded in high yields (86-98%) with excellent enantioselectivities of up to 99% ee. This method provides a straightforward strategy for the efficient synthesis of chiral multinitrogen polyheterocyclic compounds.

View Article and Find Full Text PDF

A novel convenient 2-step synthesis of substituted pyrido[1,2-]indoles is developed starting from easily available pyrylium tetrafluoroborates and -bromoanilines. A conversion of the pyrylium tetrafluoroborates to pyridinium ones followed by their palladium catalyzed intramolecular cyclization allows the formation of 24 examples of N-fused heterocycles. A one-pot two-stage cyclization procedure was developed.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!