Formation of zwitterionic salts via three-component reaction of benzimidazolium bromides, aromatic aldehydes and 1,3-indanedione

Jin, Gong; Sun, Jing; Yan, Chao‐Guo

doi:10.1039/c6ra16838h

Cited by 10 publications

(1 citation statement)

References 62 publications

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“…[13][14][15][16] There are also some recent reports on the synthesis of Nheterocyclic zwitterions by multi-component reactions. [17][18][19][20] Here we report a new three-component reaction of pyridine, quinoline or isoquinoline derivatives with dialkyl acetylenedicarboxylate (DAAD) derivatives in the presence of barbituric or thiobarboturic acid for the synthesis of new functionalized N-heterocycle zwitterions.…”

Section: Introductionmentioning

confidence: 99%

Formation of zwitterionic salts via three-component reactions of barbituric/thiobarbituric acid, N-heterocyclic compounds and dialkyl acetylenedicarboxylates

Anary‐Abbasinejad¹,

Nejad-Shahrokhabadi²

2019

Arkivoc

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Section: Introductionmentioning

confidence: 99%

Formation of zwitterionic salts via three-component reactions of barbituric/thiobarbituric acid, N-heterocyclic compounds and dialkyl acetylenedicarboxylates

Anary‐Abbasinejad¹,

Nejad-Shahrokhabadi²

2019

Arkivoc

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Selective Construction of Spiro[indene‐2,4′‐pyrido[1,2‐a]quinolines] and Dihydroindeno[1,2‐b]pyrene via Domino Reactions of Huisgen's 1,4‐Dipoles

et al. 2018

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The three‐component reaction of quinoline, dimethyl acetylenedicarboxylate and 2‐arylidene‐1,3‐indanediones or 5‐arylidene‐N,N’‐dimethylbarbituric acids in acetonitrile at room temperature afforded polysubstituted spiro[indene‐2,4′‐pyrido[1,2‐a]quinolines] or spiro[pyrido[1,2‐a]quinoline‐4,5′‐pyrimidines] in high yields and with high diastereoselectivity. However, the similar reaction of dimethyl acetylenedicarboxylate with 2‐arylidene‐1,3‐indanediones in the presence of 4‐Dimethylaminopyridine (DMAP) gave unexpected dihydroindeno[1,2‐b]pyrene derivatives in satisfactory yields. This three‐component reaction containing quinoline might be the most sustainable reaction without release any waste.

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Multicomponent Reaction for Selective Synthesis of Spiro[indene‐2,7′‐isoquinoline] and 1,2,8,8 a‐Tetrahydroisoquinoline Derivatives

2019

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The piperidine promoted three‐component reaction of N‐alkylpiperidin‐4‐ones, malononitrile and 2‐arylidene‐1,3‐indanediones in ethanol selectively resulted in the spiro[indene‐2,7′‐isoquinoline] and the ring‐opened cis‐ or trans‐1,2,8,8a‐tetrahydroisoquinoline derivatives at room temperature or at the elevated temperature. However, the four‐component reaction N‐alkylpiperidin‐4‐ones, malononitrile, aromatic aldehydes and 1,3‐indanedione in refluxing ethanol mainly afforded ring‐opened cis‐1,2,8,8a‐tetrahydroisoquinoline derivatives in good yields and with high diastereoselectivity. A plausible domino reaction mechanism was proposed for the formation of the different polycyclic products.

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Formation of zwitterionic salts via three-component reaction of benzimidazolium bromides, aromatic aldehydes and 1,3-indanedione

Abstract: The three-component reaction in ethanol in the presence of triethylamine as base catalyst resulted in the unusual charge-separated zwitterionic salts in good yields.

Cited by 10 publications

References 62 publications

Formation of zwitterionic salts via three-component reactions of barbituric/thiobarbituric acid, N-heterocyclic compounds and dialkyl acetylenedicarboxylates

Formation of zwitterionic salts via three-component reactions of barbituric/thiobarbituric acid, N-heterocyclic compounds and dialkyl acetylenedicarboxylates

Selective Construction of Spiro[indene‐2,4′‐pyrido[1,2‐a]quinolines] and Dihydroindeno[1,2‐b]pyrene via Domino Reactions of Huisgen's 1,4‐Dipoles

Multicomponent Reaction for Selective Synthesis of Spiro[indene‐2,7′‐isoquinoline] and 1,2,8,8 a‐Tetrahydroisoquinoline Derivatives

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