Synthesis of 4,5-Diaminopyrrolo[1,2-a]quinoline Derivatives by a Lewis Acid Catalyzed Reaction of 2-(Pyrrol-1-yl)benzaldimines with Isocyanides

Kobayashi, Kazuhiro; Himei, Yasutoshi; Izumi, Yuichi; Fukamachi, Shuhei; Morikawa, Osamu; Konishi, Hisatoshi

doi:10.3987/com-06-10963

Cited by 4 publications

(2 citation statements)

References 6 publications

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“…68 The same authors also reported the reaction using primary amines in the presence of BF 3 •EtO 2 as the activating agent. 69 An aldehyde bearing an enamide (174) was a perfect substrate to intramolecularly intercept the nitrilium ion in a multicomponent reaction with a primary aliphatic amine 98 and an isocyanide 2 to form imidazolinium ion 175 (Scheme 53). The presence of Zn(OTf) 2 as an activator, both of the carbonyl and the imine group, was necessary for higher yields and reduced reaction times.…”

Section: Review Syn Thesismentioning

confidence: 99%

Interrupted Ugi and Passerini Reactions: An Underexplored Treasure Island

et al. 2018

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The formation of the key short-lived intermediate nitrilium ion in the Passerini and Ugi reactions was recognized early in the discovery of these two-multicomponent transformations. Surprisingly, the idea of intramolecularly intercepting it, eluding the attack by the carboxylate, and thus interrupting the normal course of the reaction, was missed by chemists for several decades. In this review we describe, in an exhaustive manner, the reported synthetic approaches, which can be categorized as interrupted Passerini/Ugi reactions. Besides, the clear goal of this review is to show the potential of these transformations, whilst highlighting the underexplored combinations of reagents toward the identification of novel interrupted Passerini/Ugi reactions.1 Introduction2 The Interrupted Ugi Reaction2.1 The Interrupting Functional Group is Present on the Amine Reactant2.2 The Interrupting Functional Group is Present on the Isocyanide Reactant2.3 The Interrupting Functional Group is Present on the Carbonyl Reactant3 The Interrupted Passerini Reaction3.1 The Interrupting Functional Group is Present on the Carbonyl Reactant3.2 The Interrupting Functional Group is Present on the Isocyanide Reactant4 Conclusions and Future Outlook

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Section: Review Syn Thesismentioning

confidence: 99%

Interrupted Ugi and Passerini Reactions: An Underexplored Treasure Island

et al. 2018

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“…1 In addition, we demonstrated that 3,4diaminopyrrolo[1,2-a]quinoline derivatives could be obtained by reactions of 2-(pyrrol-1yl)benzaldehydes with secondary amine hydrochlorides in the presence of isocyanides, 2 or by boron trifluoride catalyzed reactions of 2-(pyrrol-1-yl)benzaldimines with isocyanides. 3 We became interested in the development of a new and facile method for preparing pyrrolo[1,2-a]quinolines carrying no substituent at all of the 1-to 5-positions. Although a number of syntheses of pyrrolo[1,2-a]quinoline derivatives have recently been reported, 4 there have been only a few reports on the synthesis of this class of pyrrolo[1,2-a]quinolines, 5 The methods involve multi-step sequences and/or rare metal-catalyzed reactions.…”

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confidence: 99%