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Journal ArticleDOI

Diversity Oriented Syntheses of Conventional Heterocycles by Smart Multi Component Reactions (MCRs) of the Last Decade

20 Jan 2012-Molecules (MDPI AG)-Vol. 17, Iss: 1, pp 1074-1102
TL;DR: A collection of smart multicomponent reactions (MCRs) with continuative post condensation cyclizations (PCCs) is presented to construct conventional three- to seven-membered heterocyclic compounds in diversity oriented syntheses (DOS).
Abstract: A collection of smart multicomponent reactions (MCRs) with continuative post condensation cyclizations (PCCs) is presented to construct conventional three- to seven-membered heterocyclic compounds in diversity oriented syntheses (DOS). These will provide a high degree of applying economical and ecological advantages as well as of practicability. Water, ionic liquids, and solvent-less syntheses as well as use of various forms of energy as microwave and ultrasonic irradiation are examined and discussed.

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Citations
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Journal ArticleDOI
TL;DR: This work describes the progress made in this area in the period between mid-2009 and the end of 2013 by describing the ready availability of suitably substituted and functionalized pyrrole derivatives.
Abstract: 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.

541 citations

Journal ArticleDOI
TL;DR: In this paper, a review summarizes recent results of multicomponent reactions obtained in unconventional media including water, ionic liquids, polyethylene glycol and bio-based solvents.

498 citations

Journal ArticleDOI
TL;DR: This tutorial review focuses on Isocyanides various applications in chemical synthesis, and the wide range of systems that can be efficiently prepared using this strategy are documented.
Abstract: Isocyanides possess a rich history in the world of synthetic chemistry. Recently the scope of this already versatile class of reagent has been expanded into its use in palladium-catalysed cascade sequences. The scope of this type of reaction is explored in depth and this tutorial review focuses on its various applications in chemical synthesis, and the wide range of systems that can be efficiently prepared using this strategy are documented.

266 citations

Journal ArticleDOI
TL;DR: Multicomponent reactions promoted by mechanical energy are critically reviewed and new ideas are proposed to improve the understanding of these reactions.
Abstract: Historically, the use of mechanochemical methods in synthesis has been almost negligible, but their perception by the synthetic community has changed in recent years and they are on their way to becoming mainstream. However, the hybridization of mechanochemical synthesis with methodologies designed to increase synthetic efficiency by allowing the generation of several bonds in a single operation has taken off only recently, but it already constitutes a very promising approach to sustainable chemistry. In this context, we provide in this Perspective a critical summary and discussion of the main known synthetic methods based on mechanochemical multicomponent reactions.

167 citations

References
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Book
30 Sep 1997
TL;DR: In this article, the CHEC III is organized in 15 volumes and closely follows the organization used in the previous edition: Volumes 1 and 2: Cover respectively three and four-membered heterocycles, together with all fused systems containing a three- or four-measured heterocyclic ring.
Abstract: CHEC III is organized in 15 Volumes and closely follows the organization used in the previous edition: Volumes 1 and 2: Cover respectively three- and four-membered heterocycles, together with all fused systems containing a three- or four-membered heterocyclic ring. Volume 3: Five-membered rings with one heteroatom together with their benzo- and other carbocyclic-fused derivatives. Volumes 4, 5 and 6: Cover five-membered rings with two heteroatoms, and three or more heteroatoms, respectively, each with their fused carbocyclic compounds. Volumes 7, 8 and 9: Dedicated to six-membered rings with one, two, and more than two heteroatoms, respectively, again with the corresponding fused carbocylic compounds. Volumes 10, 11 and 12: Cover systems containing at least two directly fused heterocyclic five- and/or six-membered rings: of these Volume 10 deals with bi-heterocyclic rings without a ring junction heteroatom, and Volume 11 deals with 5:5 and 5:6 fused rings systems with at least one ring junction nitrogen, while Volume 12 is devoted to all other systems of five and/or six-membered fused or spiro heterocyclic rings with ring junction heteroatoms. Volumes 13 and 14: Seven-membered and larger heterocyclic rings including all their fused derivatives (except those containing three- or four-membered heterocyclic rings which are included in Volume 1 and 2, respectively). Volume 15: Author, ring and subject indexes.

8,174 citations


"Diversity Oriented Syntheses of Con..." refers background in this paper

  • ...Multi Component Reaction (MCR) chemistry [1,2] applied to the synthesis of heterocycles [3–5] with all its variations and extensions has undergone an enormous and meaningful upturn....

    [...]

Journal ArticleDOI
TL;DR: The preparation of urea by Wöhler constituted a landmark achievement in organic chemistry, and it laid the ground for the early days of target-oriented organic synthesis, a task deemed inconceivable by early practitioners.
Abstract: The preparation of urea by Wöhler constituted a landmark achievement in organic chemistry, and it laid the ground for the early days of target-oriented organic synthesis.1 Since then, significant progress has been achieved in this discipline; many powerful single bond forming reactions and asymmetric variants have been developed. These discoveries have paved the way for the stereoselective assembly of complex organic molecules, a task deemed inconceivable by early practitioners. A great many strategies were invented by chemists in order to facilitate the synthesis of complex natural products.2 One avenue in emulating nature’s efficiency would * To whom correspondence should be addressed. E-mail: dennis.hall@ ualberta.ca. † Novartis Institute for Biomedical Research. ‡ Department of Chemistry, University of Alberta. Chem. Rev. 2009, 109, 4439–4486 4439

1,374 citations

Journal ArticleDOI
TL;DR: Although the distinct goals of DOS do not permit the application of retrosynthetic concepts and thinking, these foundations are being built on, by using parallel logic, to develop a complementary procedure known as forward-Synthetic analysis, which facilitates synthetic planning, communication, and teaching in this evolving discipline.
Abstract: In contrast to target-oriented synthesis (TOS) and medicinal or combinatorial chemistry, which aim to access precise or dense regions of chemistry space, diversity-oriented synthesis (DOS) populates chemical space broadly with small-molecules having diverse structures. The goals of DOS include the development of pathways leading to the efficient (three- to five-step) synthesis of collections of small molecules having skeletal and stereochemical diversity with defined coordinates in chemical space. Ideally, these pathways also yield compounds having the potential to attach appendages site- and stereoselectively to a variety of attachment sites during a post-screening, maturation stage. The diverse skeletons and stereochemistries ensure that the appendages can be positioned in multiple orientations about the surface of the molecules. TOS as well as medicinal and combinatorial chemistries have been advanced by the development of retrosynthetic analysis. Although the distinct goals of DOS do not permit the application of retrosynthetic concepts and thinking, these foundations are being built on, by using parallel logic, to develop a complementary procedure known as forward-synthetic analysis. This analysis facilitates synthetic planning, communication, and teaching in this evolving discipline.

1,218 citations


"Diversity Oriented Syntheses of Con..." refers background in this paper

  • ...Diversity of products is increasing by both versatile and smart MCRs and many consecutive further reactions like versatile domino-reactions and post-condensation-cyclisations (PCCs) [12,13]....

    [...]

Journal ArticleDOI
TL;DR: An overview of general strategies that allow the design of novel multicomponent reactions is presented and the challenges and opportunities for the future are discussed.
Abstract: Multicomponent reactions have become increasingly popular as tools for the rapid generation of small-molecule libraries. However, to ensure sufficient molecular diversity and complexity, there is a continuous need for novel reactions. Although serendipity has always played an important role in the discovery of novel (multicomponent) reactions, rational design strategies have become much more important over the past decade. In this Review, we present an overview of general strategies that allow the design of novel multicomponent reactions. The challenges and opportunities for the future will be discussed.

1,036 citations

Journal ArticleDOI
Bruce Ganem1
TL;DR: This Account provides several examples that illustrate the use of SRR with known MCRs as starting points for synthetic innovation in this area, and explores strategies for engineering improvements into known M CRs, either by increasing the dimensionality, broadening the scope of useful input structures, or both.
Abstract: By generating structural complexity in a single step from three or more reactants, multicomponent reactions (MCRs) make it possible to synthesize target compounds with greater efficiency and atom economy. The history of such reactions can be traced to the mid-19th century when Strecker first produced α-aminonitriles from the condensation of aldehydes with ammonia and hydrogen cyanide. Recently, academic chemists have renewed their interest in MCRs. In part, the pharmaceutical industry has fueled this resurgence because of the growing need to assemble libraries of structurally complex substances for evaluation as lead compounds in drug discovery and development programs. The application of MCRs to that increasingly important objective remains limited by the relatively small number of such reactions that can be broadly applied to prepare biologically relevant or natural-product-like molecular frameworks. We were interested in applying logic-based approaches, such as our single reactant replacement (SRR) app...

966 citations