Late transition metal-catalyzed hydroamination and hydroamidation.

Pyrrole is one of the most important one-ring heterocycles. The ready availability of suitably substituted and functionalized pyrrole derivatives is essential for the progress of many branches of science, including biology and materials science. Access to this key heterocycle by multicomponent routes is particularly attractive in terms of synthetic efficiency, and also from the environmental point of view. We update here our previous review on this topic by describing the progress made in this area in the period between mid-2009 and the end of 2013.

Recent advances in the synthesis of pyrroles by multicomponent reactions

Synthesis of heterocycles from alkyl 3-(dimethylamino)propenoates and related enaminones.

Multicomponent reactions have gained significant importance as a tool for the synthesis of a wide variety of useful compounds, including pharmaceuticals. In this context, the multiple component approach is especially appealing in view of the fact that products are formed in a single step, and the diversity can be readily achieved simply by varying the reacting components. The eco-friendly, solvent-free multicomponent approach opens up numerous possibilities for conducting rapid organic synthesis and functional group transformations more efficiently. Additionally, there are distinct advantages of these solvent-free protocols since they provide reduction or elimination of solvents thereby preventing pollution in organic synthesis “at source”. The chemo-, regio- or stereoselective synthesis of high-value chemical entities and parallel synthesis to generate a library of small molecules will add to the growth of multicomponent solvent-free reactions in the near future. In this review we summarized the results reported mainly within the last 10 years. It is quite clear from the growing number of emerging publications in this field that the possibility to utilize multicomponent technology allows reaction conditions to be accessed that are very valuable for organic synthesis. Therefore, diversity oriented synthesis (DOS) is rapidly becoming one of the paradigms in the process of modern drug discovery. This has spurred research in those fields of chemical investigation that lead to the rapid assembly of not only molecular diversity, but also molecular complexity. As a consequence multi-component as well as domino or related reactions are witnessing a new spring.

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Recent developments in solvent-free multicomponent reactions: a perfect synergy for eco-compatible organic synthesis

Cyclizations of Alkynes: Revisiting Baldwin’s Rules for Ring Closure

Cultivating the Passion to Build Heterocycles from 1,2‐Diaza‐1,3‐dienes: the Force of Imagination

A new and efficient synthesis of polysubstituted pyrroles by a sequential one-pot three-component reaction between primary aliphatic amines, active methylene compounds, and 1,2-diaza-1,3-dienes (DDs) is reported. The reactions were performed without catalyst and under solvent-free conditions with complete control of pathway selectivity. Notably, the ready availability of the starting materials and the high level of practicability of the reaction and work up make this approach an attractive complementary method for access to unknown polysubstituted pyrroles.

Synthesis of functionalized pyrroles via catalyst- and solvent-free sequential three-component enamine-azoene annulation.

Effect of Metal Ions in Organic Synthesis; Part XXIII. Easy and High-Yield Direct Synthesis of 3-Aminocarbonyl-1-ureidopyrroles by the Copper(II) Chloride-Catalyzed Reaction of Aminocarbonylazoalkenes with 3-Oxoalkanamides

A novel and convenient protocol for synthesis of pyridazines.

Effect of Metal Ions in Organic Synthesis; Part XXIV. Facile One-Flask Synthesis of 1-Alkoxycarbonylamino-3-aminocarbonylpyrroles by Reaction of Alkoxycarbonylazoalkenes with 3-Oxoalkanamides under Copper(II) Chloride Catalysis

Stefania Santeusanio

Papers

Cultivating the Passion to Build Heterocycles from 1,2‐Diaza‐1,3‐dienes: the Force of Imagination

Synthesis of functionalized pyrroles via catalyst- and solvent-free sequential three-component enamine-azoene annulation.

Effect of Metal Ions in Organic Synthesis; Part XXIII. Easy and High-Yield Direct Synthesis of 3-Aminocarbonyl-1-ureidopyrroles by the Copper(II) Chloride-Catalyzed Reaction of Aminocarbonylazoalkenes with 3-Oxoalkanamides

A novel and convenient protocol for synthesis of pyridazines.

Effect of Metal Ions in Organic Synthesis; Part XXIV. Facile One-Flask Synthesis of 1-Alkoxycarbonylamino-3-aminocarbonylpyrroles by Reaction of Alkoxycarbonylazoalkenes with 3-Oxoalkanamides under Copper(II) Chloride Catalysis