The Seven‐Component Reaction<sup>**</sup>

Dömling, Alexander; Ugi, Ivar

doi:10.1002/anie.199305631

Cited by 131 publications

(53 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…9,10 Considering the synthetic breadth of this 7CR only 3 components are highly variable. However, the field of isonitrile based MCRs has been and is still the source of many elegant novel synthetic routes to all kinds of molecules (see reviews given by Ugi 11 and Torroba…”

Section: Methodsmentioning

confidence: 99%

Discovery of New Multi Component Reactions with Combinatorial Methods

Weber

Illgen

Almstetter

1999

Synlett

570

191

View full text Add to dashboard Cite

Abstract:The discovery of novel chemical reactions or reaction sequences that are able to generate useful chemical products may be regarded as the heart of organic chemistry. We present here concepts and methods on how to find and explore new multi component reactions, especially with automated combinatorial methods. This "combinatorial reaction finding" provides also a powerful tool to the understanding of the rules of organic chemistry, especially structure-reactivity relationships.

show abstract

Section: Methodsmentioning

confidence: 99%

Discovery of New Multi Component Reactions with Combinatorial Methods

Weber

Illgen

Almstetter

1999

Synlett

570

191

View full text Add to dashboard Cite

show abstract

“…[23] The N-(cyanomethyl)amide intermediate 23 was accessed via a second three-component reaction. [24] Here the authors made use of the difference in reactivity of the two isocyanides in 2,5-diisocyanopentanamide (20) to produce compound 23 in good yield, carrying an isocyanide handle for the subsequent MCR. Multicomponent products 19 and 23 could be formed either in separate reaction vessels (sequential manner) or in a single reaction vessel.…”

Section: Union Of Multicomponent Reactionsmentioning

confidence: 99%

“…[4] An important subgroup of MCRs is the so-called unions of MCRs, where an MCR is combined with a secondary reaction, e.g., an MCR, in the same flask, enhancing the diversity and potential usefulness of the reactions. [5] MCRs bridge one-and two-component reactions with polymerizations, where one or several starting materials combine repetitively to form a polymer of varying length. The majority of organic textbook chemistry consists of one-and two-component reactions and polymerizations.…”

Section: Multicomponent Reactionsmentioning

confidence: 99%

“…[20] The union of MCRs is a strategy for the rational design of novel MCRs combining two (or more) different types of MCRs in a one-pot process. The presence of orthogonal reactive groups in the product of the primary MCR, which is either formed during the primary MCR or present in one of the inputs, allows the union with the secondary MCR.…”

Section: Union Of Multicomponent Reactionsmentioning

confidence: 99%

See 1 more Smart Citation

Multicomponent Reactions, Union of MCRs and Beyond

Zarganes‐Tzitzikas

Chandgude

Dömling

2015

The Chemical Record

Self Cite

230

142

View full text Add to dashboard Cite

Multicomponent reactions (MCRs), which are located between one- and two-component and polymerization reactions, provide a number of valuable conceptual and synthetic advantages over stepwise sequential approaches towards complex and valuable molecules. To address current limitations in the number of MCRs and the resulting scaffolds, the concept of union of MCRs was introduced two decades ago by Dömling and Ugi and is rapidly advancing, as is apparent by several recently published works. MCR technology is now widely recognized for its impact on drug discovery projects and is strongly endorsed by industry in addition to academia. Clearly, novel scaffolds accessible in few steps including MCRs will further enhance the field of applications. Additionally, broad expansion of MCR applications in fields such as imaging, materials science, medical devices, agriculture, or futuristic applications in stem cell therapy and theragnostics or solar energy and superconductivity are predicted.

show abstract

“…The combination of multicomponent reactions (MCR 2 ), [13][14][15] which combines different types of MCRs in one pot process inheriting the high selectivity, efficiency, and atom economy of MCR, has gained more and more attention, since Dömling and Ugi reported the first MCR 2 of a modified four-component reaction (4CR) and the Ugi 4CR. 16) However, most of the reported MCR 2 cases are limited in isonitrile based multicomponent reactions. [17][18][19][20][21] Hence in this work, we report a one-pot, three-component reaction for the synthesis of 4H-pyran derivatives through the reaction of acetoacetanilide derivatives with cyanomethylene derivatives and aromatic aldehydes.…”

mentioning

confidence: 99%

Multicomponent Reactions of Acetoacetanilide Derivatives with Aromatic Aldehydes and Cyanomethylene Reagents to Produce 4<i>H</i>-Pyran and 1,4-Dihydropyridine Derivatives with Antitumor Activities

Azzam

Mohareb

2015

Chem. Pharm. Bull.

View full text Add to dashboard Cite

The multi-component reaction of either acetoacetanilide derivative 1a or b with any of the aldehyde derivatives 2a-d and malononitrile 3 in the presence of triethylamine as a catalyst gave the 4H-pyran derivatives 4a-g, respectively. Carrying the same reaction but using a catalytic amount of ammonium acetate gave the 1,4-dihydropyridine derivatives 5a-f, respectively. The use of ethyl cyanoacetate instead of malononitrile in the presence of a catalytic amount of triethylamine gave the 4H-pyran derivatives 7a-d, respectively. Compound 4e was used to synthesize 1,4-dihydropyridine 9a-c and arylhydraone 11a-e derivatives were synthesized from 4a and e. The anti-tumor evaluations of the newly synthesized products were tested against six human cancer and normal cell lines. The results showed that compounds 4a, b, f, 5d, f, 9 and 11a-d had optimal cytotoxic effect against cancer cell lines with IC 50 <550 nM. The toxicity of the most active compounds was further measured against shrimp larvae.Key words 4H-pyran; 1,4-dihydropyridine; cyanomethylene; cytotoxicity Multicomponent reactions (MCRs) are one-pot reactions employing more than two starting materials, e.g. 3, 4, ... , 7, where most of the atoms of the starting materials are incorporated in the final product.1) Several descriptive tags are regularly attached to MCRs they are atom economic, e.g. the majority if not all of the atoms of the starting materials are incorporated in the product; they are efficient, e.g. they efficiently yield the product since the product is formed in onestep instead of multiple sequential steps; they are convergent, e.g. several starting materials combine in one reaction to form the product; they exhibit a very high bond-forming-index (BFI), e.g. several non-hydrogen atom bonds are formed in one synthetic transformation.2,3) Therefore MCRs are often a useful alternative to sequential multistep synthesis.In view of the increasing interest in the preparation of a large variety of heterocyclic compound libraries, the development of new synthetically valuable MCRs with several diversity points remains a challenge for both academic and industrial institutions.4) 4H-Pyran and its derivatives are an important class of heterocyclic compounds possessing broad biological activities, such as anti-inflammatory, 5) analgesic, 6) antioxidant,antiamoebic 11) and oral analgesic. 12) From the aforementioned reports, it seemed that the development of an efficient, rapid, and clean synthetic route towards focused libraries of such compounds is of great importance to both medicinal and synthetic chemists. The combination of multicomponent reactions (MCR 2 ), [13][14][15] which combines different types of MCRs in one pot process inheriting the high selectivity, efficiency, and atom economy of MCR, has gained more and more attention, since Dömling and Ugi reported the first MCR 2 of a modified four-component reaction (4CR) and the Ugi 4CR.16) However, most of the reported MCR 2 cases are limited in isonitrile based multicomponent reactions. [17][18][19][20]...

show abstract

The Seven‐Component Reaction^**

Cited by 131 publications

References 15 publications

Discovery of New Multi Component Reactions with Combinatorial Methods

Discovery of New Multi Component Reactions with Combinatorial Methods

Multicomponent Reactions, Union of MCRs and Beyond

Multicomponent Reactions of Acetoacetanilide Derivatives with Aromatic Aldehydes and Cyanomethylene Reagents to Produce 4<i>H</i>-Pyran and 1,4-Dihydropyridine Derivatives with Antitumor Activities

Contact Info

Product

Resources

About

The Seven‐Component Reaction**

Cited by 131 publications

References 15 publications

Discovery of New Multi Component Reactions with Combinatorial Methods

Discovery of New Multi Component Reactions with Combinatorial Methods

Multicomponent Reactions, Union of MCRs and Beyond

Multicomponent Reactions of Acetoacetanilide Derivatives with Aromatic Aldehydes and Cyanomethylene Reagents to Produce 4<i>H</i>-Pyran and 1,4-Dihydropyridine Derivatives with Antitumor Activities

Contact Info

Product

Resources

About

The Seven‐Component Reaction^**