Diels−Alder Reaction of 2-Amino-Substituted Furans as a Method for Preparing Substituted Anilines

1997 ◽  
Vol 62 (12) ◽  
pp. 4088-4096 ◽  
Author(s):  
Albert Padwa ◽  
Martin Dimitroff ◽  
Alex G. Waterson ◽  
Tianhua Wu
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Substituted Anilines ◽  
Diels Alder Reaction ◽  
Substituted Furans

4-Aryl-3-substituted Furans

1994 ◽  
Vol 59 (12) ◽  
pp. 2721-2726 ◽  
Author(s):  
Jarmila Štetinová ◽  
Ján Leško ◽  
Miloslava Dandárová ◽  
Rudolf Kada ◽  
Roman Koreň
Keyword(s):  
Thermal Decomposition ◽  
Triple Bond ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Substituted Furans

4-Aryl-3-substituted furans IIIa - IIId were prepared by Diels Alder reaction of 4-phenyloxazole (I) with compounds IIa - IId, containing an activated triple bond, and subsequent thermal decomposition of the cycloadduct.

Influence of Lewis acids on the Diels–Alder reaction. II. Rearrangement of 1- and 1,4-substituted diethyl 7-oxabicyclo[2•2•1]2,5-heptadiene-2,3-dicarboxylate adducts to 4- and 4,6-substituted diethyl 3-hydroxyphthalates

1969 ◽  
Vol 47 (23) ◽  
pp. 4319-4326 ◽  
Author(s):  
A. W. McCulloch ◽  
B. Stanovnik ◽  
D. G. Smith ◽  
A. G. McInnes
Keyword(s):  
Lewis Acids ◽  
Room Temperature ◽  
Alder Reaction ◽  
Diels Alder ◽  
Substituted Phenols ◽  
Aryl Substituent ◽  
Diels Alder Reaction ◽  
Step Procedure ◽  
Direct Formation ◽  
Substituted Furans

Direct formation of 4- or 4,6-alkyl and aryl substituted diethyl 3-hydroxyphthalates from the correspondingly substituted Diels–Alder adducts of 2- or 2,5-substituted furans and diethyl acetylenedicarboxylate is promoted by AlCl3 in CH2Cl2 at room temperature. The first adduct of 2,5-diphenylfuran to be isolated has been obtained from the same reaction at −20°. The aromatic compounds can be obtained alternatively by treating the adducts with BF3 or H2SO4: where the adducts can be prepared by conventional means this two-step procedure has resulted in greatly improved yields. Adducts of furan and furfuryl alcohol are similarly converted to substituted phenols. HCl effected conversion only in the case of adducts carrying a bridgehead aryl substituent; in all other cases HCl added to the substituted double bond. The mechanism of the adduct rearrangement is discussed.

Imino Diels–Alder reaction — An efficient synthetic protocol for 2-methyl-4-substituted tetrahydroquinolines catalyzed by copper dipyridine dichloride

2010 ◽  
Vol 88 (5) ◽  
pp. 443-452 ◽  
Author(s):  
C. S. Kavitha ◽  
K. M. Hosamani ◽  
R. S. Harisha
Keyword(s):  
Elemental Analysis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Reusable Catalyst ◽  
Substituted Anilines ◽  
H Nmr ◽  
Diels Alder Reaction ◽  
First Time ◽  
C Nmr

For the first time, copper dipyridine dichloride (CuPy2Cl2) is used as an efficient and reusable catalyst for the imino Diels–Alder reaction of para-substituted anilines with N-vinylpyrrolidinone, N-vinylcarbazole, and N-vinylcaprolactam in acetonitrile to afford the corresponding 2-methyl-4-substituted-1,2,3,4-tetrahydroquinoline derivatives in excellent yields with good purity. The products were characterized by FTIR, 1H NMR, 13C NMR, MS, and elemental analysis.

IntraMolecular Diels–Alder Reactions of Vinylarenes and Alkynyl Arenes (the IMDAV Reaction)

Synthesis ◽  
2021 ◽  
Author(s):  
Fedor I. Zubkov ◽  
Gaddam Krishna ◽  
Dmitry G. Grudinin ◽  
Eugeniya V. Nikitina
Keyword(s):  
Multiple Bond ◽  
Alder Reaction ◽  
Diels Alder ◽  
Bioactive Molecules ◽  
Second Stage ◽  
Diels Alder Reaction ◽  
Naturally Occurring ◽  
Benzene Rings ◽  
Substituted Furans ◽  
Classical Mechanism

AbstractThis comprehensive review summarizes the published literature data concerning the intramolecular Diels–Alder reactions of vinylarenes (the IMDAV reaction) and alkynyl arenes from 1970 to 2019, and covers mainly intramolecular [4+2] cycloaddition reactions of vinyl- or acetylene-substituted furans, thiophenes, pyrroles, indoles, imidazoles, benzenes, and naphthalenes, in which the unsaturated substituent is linked directly to an arene moiety. The selected area of the Diels–Alder reaction differs from other forms of [4+2] cycloadditions due to the uniqueness of the diene fragment, which, along with an exocyclic multiple bond, includes the double bond of an aromatic or heteroaromatic nucleus in its system. Thus, during the formation of the [4+2] cycloaddition intermediate, the aromaticity of furan, thiophene and even benzene rings is broken, leading, as a rule, to the formation of heterocyclic structures rarely accessible by other methods, in contrast to the majority of intermolecular Diels–Alder reactions, with the highest degree of chemo-, regio-, and diastereoselectivity. Therefore, the IMDAV approach is often used for the synthesis of naturally occurring and bioactive molecules, which are also discussed in this review alongside other applications of this reaction. Whenever possible, we have tried to avoid examples of radical, photochemical, oxidative, precious-metal-complex-catalyzed cyclizations and other types of formal [4+2] cycloadditions, focusing on thermal Diels–Alder reactions in the first step, according to the classical mechanism. The second stage of the process, aromatization, is unique for many initial substrates, and hence considerable attention in this overview is given to the detailed description of the reaction mechanisms.1 Introduction2 IMDAV Reactions of Vinylfurans2.1 Alkenes as Internal Dienophiles2.2 Alkynes and Allenes as Internal Dienophiles3 IMDAV Reactions of Vinylthiophenes3.1 Alkenes as Internal Dienophiles3.2 Alkynes as Internal Dienophiles4 IMDAV Reactions of Vinylbenzothiophenes5 IMDAV Reactions of Vinylpyrroles6 IMDAV Reactions of Vinylindoles6.1 Alkenes as Internal Dienophiles6.2 Alkynes as Internal Dienophiles7 IMDAV Reactions of Styrenes and Vinylnaphthalenes7.1 Alkenes as Internal Dienophiles7.2 Alkynes as Internal Dienophiles7.3 Alkynes as Internal Dienophiles in Aryl Acetylenes (the Intramolecular Dehydro Diels–Alder Reaction)8 IMDAV Reactions of Vinylimidazoles, Vinylisoxazoles and Vinylpyridines9 Conclusion10 Abbreviations

Asymmetric total syntheses of teretifolione B and methylteretifolione B via Diels-Alder reaction of optically active pyranobenzyne and substituted furans

Tetrahedron ◽  
2017 ◽  
Vol 73 (34) ◽  
pp. 5063-5071 ◽  
Author(s):  
Kazuaki Katakawa ◽  
Mika Kainuma ◽  
Katsuya Suzuki ◽  
Saori Tanaka ◽  
Takuya Kumamoto
Keyword(s):  
Alder Reaction ◽  
Optically Active ◽  
Diels Alder ◽  
Total Syntheses ◽  
Diels Alder Reaction ◽  
Substituted Furans

The Diels-Alder Reaction of 2-Ethenyl-1,4-Benzodioxin: A New and Simple Synthesis of Bisaryl Ethers

Synlett ◽  
1989 ◽  
Vol 1989 (01) ◽  
pp. 30-32
Author(s):  
Thomas V. Lee ◽  
Alistair J. Leigh ◽  
Christopher B. Chapleo
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Simple Synthesis ◽  
Diels Alder Reaction
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