The Multi-component Synthesis of Pyrroles from Cyclopropanes Using a One Pot Pd(II) Catalyzed Dehydrocarbonylation Protocol

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ISBN 13 :
Total Pages : 266 pages
Book Rating : 4.:/5 (16 download)

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Book Synopsis The Multi-component Synthesis of Pyrroles from Cyclopropanes Using a One Pot Pd(II) Catalyzed Dehydrocarbonylation Protocol by : William John Humenny

Download or read book The Multi-component Synthesis of Pyrroles from Cyclopropanes Using a One Pot Pd(II) Catalyzed Dehydrocarbonylation Protocol written by William John Humenny and published by . This book was released on 2012 with total page 266 pages. Available in PDF, EPUB and Kindle. Book excerpt: Previous work done by the Kerr group has shown that tetrahydro-1,2-oxazines can be efficiently synthesized using a three component coupling reaction between a hydroxylamine, aldehyde and cyclopropane diester. This affords the desired heterocycle efficiently with a wide variety of substitution. When one esters bears an allyl group a Tsuji dehydrocarbonylation reaction may take place resulting in the formation of a 4,5-dihydro- 1,2-oxazine. This motif contains a vinylogously acidic proton which is extremely labile and easily deprotonated. Under basic conditions this proton is removed and consequently the N-O bond is cleaved and subsequent condensation occurs forming a pyrrole. Using a sequence of chemical transformations specific pyrroles generated from the above methodology could be transformed into either BM 212 an anti-tuberculosis drug or Atorvastatin Calcium an anticholesterol drug. Each pharmaceutical will be derived using a three component coupling reaction and then conversion to a pyrrole followed by manipulations of the resulting functional groups.

Copper-Catalyzed Multi-Component Reactions

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Publisher : Springer
ISBN 13 : 9783642267017
Total Pages : 104 pages
Book Rating : 4.2/5 (67 download)

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Book Synopsis Copper-Catalyzed Multi-Component Reactions by : Yusuke Ohta

Download or read book Copper-Catalyzed Multi-Component Reactions written by Yusuke Ohta and published by Springer. This book was released on 2013-02-25 with total page 104 pages. Available in PDF, EPUB and Kindle. Book excerpt: A copper-catalyzed direct synthesis of 2-(aminomethyl)indoles by catalytic domino reaction including multi-component coupling was developed, and is the first example of a three-component indole formation without producing salts as a byproduct. Based on this reaction, a copper-catalyzed synthesis of 3-(aminomethyl)isoquinoline was accomplished which represents an unprecedented isoquinoline synthesis through a four-component coupling reaction. Following these results, extensive application studies using one-pot palladium-, acid-, or base-promoted cyclization revealed that indole- or isoquinoline-fused polycyclic compounds can be readily synthesized through multi-component reactions. As the concept of Green Chemistry becomes ever more important, these findings may provide efficient and atom-economical approaches to the diversity-oriented synthesis of bioactive compounds containing a complex structure. This could lead to development of promising drug leads with structural complexity. The work of this thesis will go on to inspire the synthetic research of many readers.

The Multicomponent Synthesis of 2-pyrrolines Via Phospha-münchnone Cycloaddition Reactions

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Total Pages : pages
Book Rating : 4.:/5 (979 download)

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Book Synopsis The Multicomponent Synthesis of 2-pyrrolines Via Phospha-münchnone Cycloaddition Reactions by : Victoria Jackiewicz

Download or read book The Multicomponent Synthesis of 2-pyrrolines Via Phospha-münchnone Cycloaddition Reactions written by Victoria Jackiewicz and published by . This book was released on 2017 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: "This thesis describes the use of phospha-Münchnones, a new class of mesoionic azomethine ylide, in the synthesis of 2-pyrrolines. These 1,3-dipoles are accessible via a one-pot reaction of imines, acid chlorides and organophosphorous reagents, and have been shown to participate in 1,3-dipolar cycloadditions. As described in Chapter 1, numerous azomethine ylides have been shown to undergo 1,3-dipolar cycloadditions to generate 2-pyrrolines, however many of these 1,3-dipoles face issues regarding regio- and stereoselectivity, structural flexibility and/or modularity. The purpose of this study was therefore to couple the multicomponent formation of phospha-Münchnones and develop a modular, one-pot synthesis of these products. In Chapter 2, the intermolecular cycloaddition of phospha-Münchnones and alkenes is explored. The resulting 2-pyrrolines are prepared in good yields with high diastereo- and regio-selectivity. This is likely due to the presence of the phosphorous moiety that creates a large steric and electronic bias across the 1,3-dipole, allowing for the regiospecific cycloaddition of unsymmetrical alkenes to form 2-pyrrolines." --