Efficient Assembly of Iminodicarboxamides by a “Truly” Four‐Component Reaction

Khoury, Kareem; Sinha, Mantosh K.; Nagashima, Tadamichi; Herdtweck, Eberhardt; Dömling, Alexander

doi:10.1002/anie.201205366

Cited by 50 publications

(22 citation statements)

References 40 publications

(23 reference statements)

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“…18 Moreover, it constitutes the basis of several scaffolds now found in the screening decks of the European Lead Factory library. 19 The substrate scope of our in situ variant is not distinct from the original procedure using isolated isocyanides, e.g. 8.1–8.5 (Scheme 6).…”

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confidence: 89%

Efficient Isocyanide-less Isocyanide-Based Multicomponent Reactions

et al. 2015

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Isocyanides are the “Jekyll and Hyde” of organic chemistry allowing for extremely interesting transformations that are not only extremely odorous but also noxious. Therefore, an isocyanide-less isocyanide-based multicomponent reaction (IMCR) has been developed, and this protocol is expected to replace many of the old procedures in the future not only in IMCR but in other areas of organic chemistry as well.

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confidence: 89%

Efficient Isocyanide-less Isocyanide-Based Multicomponent Reactions

et al. 2015

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“…The scope of the reaction was investigated while using representative starting material of each class. The use of bifunctional starting materials allowed for cyclizing the initially formed Ugi products, such as compound 240a, whih was obtained by P-S reaction and deprotective cyclization [224].…”

Section: Scheme 66mentioning

confidence: 99%

The Pictet-Spengler Reaction Updates Its Habits

et al. 2020

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The Pictet-Spengler reaction (P-S) is one of the most direct, efficient, and variable synthetic method for the construction of privileged pharmacophores such as tetrahydro-isoquinolines (THIQs), tetrahydro-β-carbolines (THBCs), and polyheterocyclic frameworks. In the lustro (five-year period) following its centenary birthday, the P-S reaction did not exit the stage but it came up again on limelight with new features. This review focuses on the interesting results achieved in this period (2011–2015), analyzing the versatility of this reaction. Classic P-S was reported in the total synthesis of complex alkaloids, in combination with chiral catalysts as well as for the generation of libraries of compounds in medicinal chemistry. The P-S has been used also in tandem reactions, with the sequences including ring closing metathesis, isomerization, Michael addition, and Gold- or Brønsted acid-catalyzed N-acyliminium cyclization. Moreover, the combination of P-S reaction with Ugi multicomponent reaction has been exploited for the construction of highly complex polycyclic architectures in few steps and high yields. The P-S reaction has also been successfully employed in solid-phase synthesis, affording products with different structures, including peptidomimetics, synthetic heterocycles, and natural compounds. Finally, the enzymatic version of P-S has been reported for biosynthesis, biotransformations, and bioconjugations.

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“…9 Here, we would like to report on the design of Ugi post condensation reactions leading to four highly variable heterocyclic scaffolds.…”

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confidence: 99%

“…When secondary amines were used ( 7c and 7d ), SFC traces using chiral cell OD revealed four stereoisomers in equal ratio, thus suggesting the racemization of the amino acid stereocenter by secondary amines as previously discovered. 9 (see SI-28, SI-29). …”

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Various cyclization scaffolds by a truly Ugi 4-CR

et al. 2013

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Efficient access to a large chemical space based on new scaffolds with defined 3D conformations and highly variable in the side chains is needed to find novel functional materials. Four heterocyclic scaffolds based on a four component Ugi reaction of α-amino acids, oxo components, isocyanides and primary or secondary amines suitably functionalized are described. A handful of examples are described for each scaffold.

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Efficient Assembly of Iminodicarboxamides by a “Truly” Four‐Component Reaction

Cited by 50 publications

References 40 publications

Efficient Isocyanide-less Isocyanide-Based Multicomponent Reactions

Efficient Isocyanide-less Isocyanide-Based Multicomponent Reactions

The Pictet-Spengler Reaction Updates Its Habits

Various cyclization scaffolds by a truly Ugi 4-CR

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