Formation of diverse polycyclic spirooxindoles via three-component reaction of isoquinolinium salts, isatins and malononitrile

Abstract

The triethylamine promoted three-component reaction of N-(4-nitrobenzyl), N-ethoxycarbonylmethylisoquinolinium bromide, isatins and malononitrile in ethanol afforded spiro[indoline-3,2′-pyrrolo[2,1-a]isoquinolines] in good yields and with high diastereoselectivity. The similar reaction of N-cyanomethylisoquinolinium chloride mainly gave complex indolo[2″,3″:2′,3′]pyrrolo[3′,4′:4,5]pyrrolo[2,1-a]isoquinoline derivatives. However, the three-component reaction of N-cyanomethylisoquinolinium chloride, isatins and ethyl cyanoacetate mainly resulted in functionalized spiro[indoline-3,8′-pyrido[2′,3′:4,5]pyrrolo[2,1-a]isoquinolines].

A straightforward, environmentally beneficial synthesis of spiro[diindeno[1,2-b:2′,1′-e]pyridine-11,3′-indoline]-2′,10,12-triones mediated by a nano-ordered reusable catalyst

“…Such methodology usually satisfies rigid requirements of green chemistry and is characterized by atom-economy, synthetic convergency, simple purification protocols, and decreased usage of expensive solvents and reagents 1 – 12 . In recent years, the multicomponent reaction strategy has been applied for the synthesis of spirooxindoles and other privileged isatine derivatives 13 – 20 .…”

Molecular Diversity of 1,3‐Dipolar Cycloaddition of Quinolinium Ylides with Isatylidene Malononitriles

“…According to our previously established reaction conditions for isoquinolinium salts with isatylidene malononitriles, [19] an equal amount of N-ethoxycarbonylmethylquinolinium bromide and various isatylidene malononitrile were stirred in acetonitrile in the presence of triethylamine at room temperature for about twelve hours. After workup, the expected spiro[indoline-3, 2'pyrrolo[1, 2-a]quinolines] 1 a-1 f were obtained in good yields.…”

“…[18] The triethylamine promoted three-component reaction of isoquinolinium salts with isatins and malononitrile not only afforded spiro[indoline-3, 2'-pyrrolo[2, 1-a]isoquinolines], but also gave complex indolo[2'', 3'':2',3']pyrrolo [3', 4':4,5]pyrrolo [2, 1-a]isoquinoline and spiro [indoline-3, 8'-pyrido[2', 3':4,5]pyrrolo[2, 1-a]isoquinolines] in different conditions. [19] In order to further explore the fruitful chemistry of the heteroaromatic Nylides, herein we wish to report the 1,3-dipolar cycloaddition reaction of several quinolinium bromides with isatylidene malononitriles for the synthesis of functionalized spiro[indoline-3, 2'-pyrrolo[1, 2-a]quinolines] and the corresponding 2-(2-oxoindolin-3-ylidene)-2-(2-(dicyanomethylene)quinolin-1-yl) acetate derivatives.…”

Synthesis and characterization of some 1, 5-benzodiazepine derivatives from Chalcones and their use as scavengers for some heavy metals in Environmental Systems.

“…The carbonyl group is one of the strong electron-withdrawing groups, so the presence of conjugated group with the double bond C=C will weaken the effectiveness of this bond towards the electrophilic addition. However, at the same time it activates this bond towards the electron-rich reagents or nucleophiles, as a result, the double bond in alpha, beta-unsaturated compounds are ready for nucleophilic attack (5) . Diazepines are heterocyclic compounds with a seven-ring containing two nitrogen atoms, and their name depends on the position of the nitrogen atom in relation to the other nitrogen atom, as well as on the nature of the substituent groups on the ring (6) .…”