Bis(indoline-2,3-diones): versatile precursors for novel bis(2',6'-dimethyl-2-oxo-1'H-spiro[indoline-3,4'-pyridine]-3',5'-dicarbonitrile) derivatives

Abstract

Reaction of 3-aminocrotononitrile with a series of bis(indoline-2,3-diones) afforded the corresponding bis(2',6'-dimethyl-2-oxo-1'H-spiro[indoline-3,4'-pyridine]-3',5'-dicarbonitrile) derivatives in good to excellent yields.

Synthesis of novel bis(dihydropyridine) and terpyridine derivatives

“…[22][23][24][25][26] Although the synthesis of biologically interesting 1,2dihydropyridine-3,5-dicarbonitrile derivatives has been investigated in the past, [27][28][29][30][31] there is still demand for more concise and efficient elucidation of molecular structure. In connection with this finding and in continuation to our work on Michael addition, [32][33][34][35][36][37][38] multicomponent reactions, [35][36][37][39][40][41][42][43][44][45] as well as on the synthesis of bis-heterocycles, 41,[45][46][47][48][49][50][51][52][53][54] we report herein on the synthesis of novel bis(1,2-dihydropyridine-3,5dicarbonitriles) and terpyridines utilizing 2-cyanoacetamide derivatives as intermediates.…”

New Azacycles by One‐Pot Three‐Component Hantzsch‐Like Synthesis of Tetra(hexa)azacyclopenta[a]anthracenes, Tetraazaindeno[5,4‐b]fluorenes, and Oxatetraazacyclopenta[m]tetraphenes

“…As a part of our sequential work on spirocyclic oxindoles,[ 39 , 40 , 41 , 42 , 43 , 44 , 45 ] we modified the structures by replacing the aldehydes with isatin 17 to achieve the concept of molecular hybridization [46] to improve their medicinal efficacy and overcome drug resistance. [ 47 , 48 , 49 , 50 ] Thus, the reaction of isatin 17 and 7‐amino‐2‐methyl‐3‐phenylpyrazolo[1,5‐ a ]pyrimidin‐5‐one 3 with either dimedone 5 or indan‐1,3‐dione 9 leads to the formation of the spirocyclic oxindoles of the respective tetraazacyclopenta[ a ]anthracene 18 or tetraazaindeno[5,4‐ b ]fluorene 19 (Scheme 7 ).…”

“…As a part of our sequential work on spirocyclic oxindoles, [39][40][41][42][43][44][45] we modified the structures by replacing the aldehydes with isatin 17 to achieve the concept of molecular hybridization [46] to improve their medicinal efficacy and overcome drug resistance. [47][48][49][50] Thus, the reaction of isatin…”

Synthesis of heterocyclic compounds via Michael and Hantzsch reactions

“…Yang et al [75] reported the synthesis of 9,10-bis A macromolecule 41 containing 1,4polyhydropyridines was prepared by the reaction of 3, 3-benzene-1,4-diylbis(3-aminoprop-2-enenitrile) 39 with benzene-1,4-dicarbaldehyde 40a or biphenyl-4,4dicarbaldehyde 40b in glacial acetic acid at reflux (Scheme 18). [76] Abdelmoniem et al [77] has developed an effective method for synthesis of bis (2 0 ,6 0 -dimethyl-2-oxo-1 0 Hspiro[indoline-3,4 0 -pyridine]-3 0 ,5 0 dicarbonitrile) derivatives 43 by the reaction of 3-aminocrotononitrile 12 with a series of bis(indoline-2,3-diones) 42 in acetic acid at reflux (Scheme 19).…”