Intramolecular Didehydro-Diels–Alder Reaction for the Synthesis of Benzo- and Dihydrobenzo-Fused Heterocycles

2017 ◽  
Vol 19 (7) ◽  
pp. 1500-1503 ◽  
Author(s):  
Ashley E. Bober ◽  
Justin T. Proto ◽  
Kay M. Brummond
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Fused Heterocycles ◽  
Diels Alder Reaction

Aryne-Based Multicomponent Coupling Reactions

Synlett ◽  
2020 ◽  
Vol 31 (08) ◽  
pp. 750-771
Author(s):  
Daesung Lee ◽  
Sourav Ghorai
Keyword(s):  
Multicomponent Reactions ◽  
Chemical Space ◽  
Alder Reaction ◽  
Diels Alder ◽  
Coupling Reactions ◽  
Fused Heterocycles ◽  
Diels Alder Reaction ◽  
Multicomponent Coupling Reactions ◽  
Metal Catalyzed ◽  
Multicomponent Coupling

Multicomponent reactions (MCRs) constitute a powerful synthetic tool to generate a large number of small molecules with high atom economy, which thus can efficiently expand the chemical space with molecular diversity and complexity. Aryne-based MCRs offer versatile possibilities to construct functionalized arenes and benzo-fused heterocycles. Because of their electrophilic nature, arynes couple with a broad range of nucleophiles. Thus, a variety of aryne-based MCRs have been developed, the representative of which are summarized in this account.1 Introduction2 Aryne-Based Multicomponent Reactions2.1 Trapping with Isocyanides2.2 Trapping with Imines2.3 Trapping with Amines2.4 Insertion into π-Bonds2.5 Trapping with Ethers and Thioethers2.6 Trapping with Carbanions2.7 Transition-Metal-Catalyzed Approaches3 Strategies Based on Hexadehydro Diels–Alder Reaction3.1 Dihalogenation3.2 Halohydroxylation and Haloacylation3.3 Amides and Imides3.4 Quinazolines3.5 Benzocyclobutene-1,2-diimines and 3H-Indole-3-imines3.6 Other MCRs of Arynes and Isocyanides4 Conclusion

Synthesis of chromene-fused heterocycles by the Intramolecular–Diels–Alder Reaction: An overview

Tetrahedron ◽  
2021 ◽  
pp. 132524
Author(s):  
Shayan Sheykhi ◽  
Keyvan Pedrood ◽  
Massoud Amanlou ◽  
Bagher Larijani ◽  
Mohammad Mahdavi
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Fused Heterocycles ◽  
Diels Alder Reaction

An Approach to Peri-Fused Heterocycles: A Metal-Mediated Cascade Carbonylative Cyclization/Dearomatic Diels–Alder Reaction

2019 ◽  
Vol 21 (23) ◽  
pp. 9512-9515 ◽  
Author(s):  
Yang Xu ◽  
Chenyang Jiao ◽  
Juan Li ◽  
Rongqiang Tian ◽  
Zheng Duan ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Fused Heterocycles ◽  
Diels Alder Reaction

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

The intermolecular anthracene-transfer in a regiospecific antipodal C60 difunctionalization

2020 ◽  
Author(s):  
Radu Talmazan ◽  
Klaus R. Liedl ◽  
Bernhard Kräutler ◽  
Maren Podewitz
Keyword(s):  
Noncovalent Interactions ◽  
Interaction Model ◽  
Alder Reaction ◽  
Diels Alder ◽  
Stacking Interactions ◽  
Pi Stacking ◽  
Diels Alder Reaction ◽  
Double Decker ◽  
Anthracene Molecule ◽  
New Strategies

We analyze the mechanism of the topochemically controlled difunctionalization of C60 and anthracene, where an anthracene molecule is transferred from one C60 monoadduct to another one under exclusive formation of equal amounts of C60 and the difficult to make antipodal C60 bisadduct. Our herein disclosed dispersion corrected DFT studies show the anthracene transfer to take place in a synchronous retro Diels-Alder/Diels-Alder reaction: an anthracene molecule dissociates from one fullerene under formation of an intermediate, while already undergoing stabilizing interactions with both neighboring fullerenes, facilitating the reaction kinetically. In the intermediate, a planar anthracene molecule is sandwiched between two neighboring fullerenes and forms equally strong "double-decker" type pi-pi stacking interactions with both of these fullerenes. Analysis with the distorsion interaction model shows that the anthracene unit of the intermediate is almost planar with minimal distorsions. This analysis sheds light on the existence of noncovalent interactions engaging both faces of a planar polyunsaturated ring and two convex fullerene surfaces in an unprecedented 'inverted sandwich' structure. Hence, it sheds light on new strategies to design functional fullerene based materials.<br>

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