2021
DOI: 10.3762/bjoc.17.57
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Effective microwave-assisted approach to 1,2,3-triazolobenzodiazepinones via tandem Ugi reaction/catalyst-free intramolecular azide–alkyne cycloaddition

Abstract: A novel catalyst-free synthetic approach to 1,2,3-triazolobenzodiazepinones has been developed and optimized. The Ugi reaction of 2-azidobenzaldehyde, various amines, isocyanides, and acids followed by microwave-assisted intramolecular azide–alkyne cycloaddition (IAAC) gave a series of target heterocyclic compounds in moderate to excellent yields. Surprisingly, the normally required ruthenium-based catalysts were found to not affect the IAAC, only making isolation of the target compounds harder while the micro… Show more

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Cited by 18 publications
(9 citation statements)
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“…18,19 Recently the sequence of Ugi reaction, followed by other organic reactions, has been utilized successfully in the synthesis of a series of biologically useful heterocycles. [20][21][22][23][24][25][26][27][28] For example, the spirocyclic pyrrol-2-one dienones were prepared diastereoselectively by Ugi and gold-catalyzed ipso-cyclization. 20 Diverse imidazolidinone scaffolds were obtained successfully by sequential Ugi-3CR and 5-endo-trig oxidative radical cyclization.…”
Section: Figure 1 Representative Bioactive Examples Of Fused Quinazol...mentioning
confidence: 99%
“…18,19 Recently the sequence of Ugi reaction, followed by other organic reactions, has been utilized successfully in the synthesis of a series of biologically useful heterocycles. [20][21][22][23][24][25][26][27][28] For example, the spirocyclic pyrrol-2-one dienones were prepared diastereoselectively by Ugi and gold-catalyzed ipso-cyclization. 20 Diverse imidazolidinone scaffolds were obtained successfully by sequential Ugi-3CR and 5-endo-trig oxidative radical cyclization.…”
Section: Figure 1 Representative Bioactive Examples Of Fused Quinazol...mentioning
confidence: 99%
“…Реакція Дільса-Альдера з оберненою полярністю (inverse-electron demand Diels-Alder -IEDDA), відкрита у 2008 р. Дж. Фоксом з колегами, -найшвидша біоортогональна реакція [27], яка відбувається між специфічним В НТК «Інститут монокристалів» НАН України член-кореспондент НАН України Валентин Анатолійович Чебанов разом зі співробітниками розробили ефективні підходи до синтезу похідних 1,2,3-триазолобензодіазепінів, що мають психотропну активність, з використанням тандему реакцій Угі та внутрішньомолекулярного азид-алкінового циклоприєднання в умовах мікрохвильової активації [30] (рис. 7).…”
Section: баррі шарплесс (Karl Barry Sharpless)американський хімік дру...unclassified
“…19 Among them, the Ugi reaction has become extremely popular because it provides a powerful method for the preparation of structurally diverse heterocyclic compounds with a combination of post-condensation transformations. 20 For example, an operationally simple and short synthesis of dihydropyrrolo[1,2- a ]pyrazine-diones was described by a Ugi/Pictet–Spengler sequence from readily accessible starting materials. 20 a 5-Sulfamido oxazoles were also prepared by sequential Ugi and cyclodehydration reactions triggered by Burgess-type reagents under mild conditions.…”
Section: Introductionmentioning
confidence: 99%