New fluorescent indolizines and bisindolizinylethylenes

Dumitraşcu, Florea; Vasilescu, Marilena; Drăghici, Constantin; Cãproiu, Miron Teodor; Barbu, Loredana; Dumitrescu, Dan

doi:10.3998/ark.5550190.0012.a28

Cited by 9 publications

(1 citation statement)

References 11 publications

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“…Because of such an electronic structure, indolizine derivatives exhibit potential biological activities 1,2 and optical properties. [3][4][5] Therefore, numerous indolizines have been synthesized by several methods. [6][7][8] Previously, we demonstrated a synthetic method for functionalized indolizines from 2ethynylpyridines using functionalities; a nucleophilic ring nitrogen and reactive ethynyl group.…”

Section: Introductionmentioning

confidence: 99%

Investigation of a green oligomer of an indolizine

Asahara¹,

Awane²,

Muragishi³

et al. 2017

Arkivoc

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An indolizine-based oligomer was synthesized by stirring a solution of 1-(α-alkoxybenzyl)indolizine derivative in chloroform at room temperature. The oligomer was characterized as an octamer; it was the main component in the obtained mixture of oligomers. The oligomerization was accelerated by both acid and light. The green color of the oligomer under acidic conditions turned yellowish brown under basic conditions; this color change could be repeated by changing the acidic/basic conditions.

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Section: Introductionmentioning

confidence: 99%

Investigation of a green oligomer of an indolizine

Asahara¹,

Awane²,

Muragishi³

et al. 2017

Arkivoc

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One‐Pot Two‐Step Synthesis of 1‐(Ethoxycarbonyl)indolizines via Pyridinium Ylides

Allgäuer

Mayr

2013

Eur J Org Chem

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Pyridinium salts Py+‐CH2‐EWG (EWG = CO2Et, CONEt2, CN, COMe, COPh) reacted with Michael acceptors Ar‐CH=C(CO2Et)(Acc) (Acc = CO2Et, COMe, SO2Me, CONH2) at ambient temperature in the presence of base to give [3 + 2]‐cycloadducts by stepwise [3 + 2]‐cycloaddition of the intermediate pyridinium ylides. Treatment of the crude reaction mixtures with 1 equiv. of chloranil and atmospheric oxygen in the presence of sodium hydroxide gave 1‐(ethoxycarbonyl)indolizines by dehydrogenation and elimination of the acceptor group (Acc). A good yield of indolizine was also obtained from Py+‐CH2CN and iPr‐CH=C(CO2Et)2, which indicates that this method is not restricted to aromatic Michael acceptors. Structurally related isoquinolinium salts react with Michael acceptors analogously to give pyrrolo[2,1‐a]isoquinolines.

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Iodine‐Promoted Synthesis of 1‐Alkyl‐3‐aroylindolizines from N‐(Aroylmethyl)pyridinium Salts and Aliphatic Aldehydes

Tan

Yan

et al. 2013

Heteroatom Chemistry

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An effective and practical method has been developed for the diversity‐oriented synthesis of 1‐alkyl‐3‐aroylindolizines via the 1,3‐dipolar cycloaddition of pyridinium ylides and aliphatic aldehydes in the presence of molecular iodine and a catalytic amount of MnO2. The synthesis proceeds by tandem reactions involving [3+2] cycloaddition, dehydration of the cycloadduct, and dehydroaromatization. Molecular iodine served both as a catalyst and a dehydroaromatization reagent in the reaction.

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New fluorescent indolizines and bisindolizinylethylenes

Abstract: Eleven new highly fluorescent indolizines and bisindolizinyl ethylene derivatives were synthesized using azomethine ylides for 1,3-dipolar cycloaddition reactions. An investigation of the optical properties indicated a high tunable fluorescence, both in solid state and solution.

Cited by 9 publications

References 11 publications

Investigation of a green oligomer of an indolizine

Investigation of a green oligomer of an indolizine

One‐Pot Two‐Step Synthesis of 1‐(Ethoxycarbonyl)indolizines via Pyridinium Ylides

Iodine‐Promoted Synthesis of 1‐Alkyl‐3‐aroylindolizines from N‐(Aroylmethyl)pyridinium Salts and Aliphatic Aldehydes

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