A new method for the synthesis of functionalized maleimides

Alizadeh, Abdolali; Movahedi, Farnaz; Esmaili, Abbas Ali

doi:10.1016/j.tetlet.2006.04.040

Cited by 59 publications

(21 citation statements)

References 15 publications

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“…On the basis of the well-established chemistry of amines and DMAD [29–30], the reaction between 1,2-diaminobenzene and dimethyl acetylenedicarboxylate ( 2a ) affords dihydroquinoxaline 5 . Compound 5 possesses enamine character and, thus, can readily react with ethyl bromopyruvate ( 3 ) to generate the intermediate 6 .…”

Section: Resultsmentioning

confidence: 99%

A one-pot catalyst-free synthesis of functionalized pyrrolo[1,2-a]quinoxaline derivatives from benzene-1,2-diamine, acetylenedicarboxylates and ethyl bromopyruvate

Piltan

Moradi²,

Abasi³

et al. 2013

Beilstein J. Org. Chem.

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Section: Resultsmentioning

confidence: 99%

A one-pot catalyst-free synthesis of functionalized pyrrolo[1,2-a]quinoxaline derivatives from benzene-1,2-diamine, acetylenedicarboxylates and ethyl bromopyruvate

Piltan

Moradi²,

Abasi³

et al. 2013

Beilstein J. Org. Chem.

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“…Pyrrole derivatives 79a , 79b , 79c , 79d can be obtained via a simple one‐pot reaction between diethylamine ( 77 ), dialkyl acetylenedicarboxylates 1a , 1b and arylsulfonyl isocyanates 78a , 78b (Scheme ) .…”

Section: Chemistry Of Dimethyl Acetylenedicarboxylatementioning

confidence: 99%

“…The formation of pyrrole derivatives 79a , 79b , 79c , 79d can be rationalized by the following mechanism (Scheme ) .…”

Section: Chemistry Of Dimethyl Acetylenedicarboxylatementioning

confidence: 99%

Utility of Acetylenedicarboxylate in Organic Synthesis

El‐Sheref

Brown

2016

Journal of Heterocyclic Chem

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Although, recent reviews demonstrated intensively on the reactivity of dimethyl acetylenedicarboxylate (DMAD) in organic synthesis, its reactions have still get importance addition in that field. Moreover, and due to the huge amount of published literatures dealing with the reactions of DMAD, we are trying to give more focus on the important missed reactions in addition to give more light to updated publications. DMAD is an organic compound with the formula (C6H6O4), and it is a diester in which the ester groups are conjugated with a triple bond. As such, DMAD is highly electrophilic and a widely employed as a dienophile in cycloaddition reactions, like the Diels–Alder reaction. Many organic compounds specially the heterocyclic ones were prepared via its reactions.

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“…For these reasons, the design of amenable methods for the synthesis of oxazinoisoquinolines has been one major interest of synthetic organic chemists . Nowadays, multicomponent reactions (MCRs) have been met with great welcome as one of the easiest and most economical synthetic routes in comparison with other methods . During recent years, many research groups have demonstrated that the reactive zwitterions, generated from the addition of aromatic N ‐heterocycles such as pyridine, quinoline, and isoquinoline to C–C triple bond activated by electron‐withdrawing groups, can be trapped by carbonyl compounds to yield various fused [1,3] oxazines .…”

Section: Introductionmentioning

confidence: 99%