Synthesis and pyrolysis of the Diels-Alder adduct of ditropyl and dimethyl acetylenedicarboxylate

1970 ◽  
Vol 35 (11) ◽  
pp. 3902-3904 ◽  
Author(s):  
George H. Wahl ◽  
Karl. Weiss
Keyword(s):  
Diels Alder ◽  
Dimethyl Acetylenedicarboxylate ◽  
Alder Adduct

A Total Synthesis of Dimethyl 2,3-O-Isopropylidene-l-O-oxalyl-β-DL-ribo-hexofuran-5-ulosuronate

1975 ◽  
Vol 53 (18) ◽  
pp. 2701-2706 ◽  
Author(s):  
George Just ◽  
Karl Grozinger
Keyword(s):  
Total Synthesis ◽  
Title Compound ◽  
Catalytic Reduction ◽  
Major Product ◽  
Diels Alder ◽  
High Yield ◽  
Thermal Rearrangement ◽  
Dimethyl Acetylenedicarboxylate ◽  
Alder Adduct

The synthesis of the title compound 5 was accomplished by a high-yield thermal rearrangement of the ozonide (3) of dimethyl 5,6-O-isopropylidene-7-oxabicyclo[2.2.1]hept-2-ene-exo-5,6-diol-2,3-dicarboxylate (2a), which is obtained in 30% yield from the Diels–Alder adduct of furan and dimethyl acetylenedicarboxylate. Catalytic reduction of 5 gave methyl 2,3-O-iso-propylidene-β-DL-talofuranuronate (8) as the major product, accompanied by a small amount of the allo isomer 9.

Annelated furans. XI. The reactions of 2-vinylfurans with acetylenic esters

1973 ◽  
Vol 26 (5) ◽  
pp. 1059 ◽  
Author(s):  
WJ Davidson ◽  
JA Elix
Keyword(s):  
Diels Alder ◽  
Dimethyl Acetylenedicarboxylate ◽  
Acetylenic Ester ◽  
Acetylenic Esters ◽  
Methyl Propiolate ◽  
Diene System ◽  
Alder Adduct ◽  
Ene Addition

In general dimethyl acetylenedicarboxylate and methyl propiolate have been found to react with 2-vinylfurans to give the corresponding dimethyl benzofuran-4,5-di-carboxylates and methyl benzofuran-4- carboxylates respectively. In several instances dimethyl acetylenedicarboxylate did not react exclusively with the exocyclic diene system of the 2-vinylfuran and here the corresponding dimethyl 3,6-epoxy-3-vinyl-3,6-dihydrophthalates were obtained by Diels-Alder addition to the furanoid diene system. At 80� 2-vinylfuran and dimethyl acetylenedicarboxylate formed the 1 : 2 adduct (11), the formation of which can be interpreted as involving an ene addition of a second mole of the acetylenic ester to the initially formed Diels-Alder adduct.

Syntheses of Angucyclinones Related to Ochromycinone

1998 ◽  
Vol 51 (6) ◽  
pp. 515 ◽  
Author(s):  
Tomas Rozek ◽  
Wit Janowski ◽  
John M. Hevko ◽  
Edward R. T. Tiekink ◽  
Suresh Dua ◽  
...  
Keyword(s):  
Structural Study ◽  
Alder Reaction ◽  
Diels Alder ◽  
Dimethyl Acetylenedicarboxylate ◽  
X Ray ◽  
Diels Alder Reaction ◽  
Synthetic Approaches ◽  
Alder Adduct

Two synthetic approaches have been investigated for the syntheses of model angucyclinones related to ochromycinone. The first involves a Diels–Alder/Friedel–Crafts strategy in which the Diels–Alder adduct formed between dimethyl acetylenedicarboxylate and 3-ethenyl-5,5-dimethylcyclohex-2-en-1- one was converted into 6,6-dimethyl-8-oxo-5,6,7,8-tetrahydronaphthalene-1,2-dicarboxylic anhydride, which was then reacted with benzene in a Friedel–Crafts reaction. Acid-catalysed cyclization of the Friedel–Crafts products gave 3,3-dimethyl-3,4-dihydrobenz[a]anthracene-1,7,12(2H)-trione (3) in poor yield. Angucyclinones related to (3) are formed (in 40–50% overall yield) by aromatization of the adduct formed between the appropriate 1,4-naphthoquinone and 3-[(E)-2-methoxyethenyl]- 5,5-dimethylcyclohex-2-en-1-one (this dienone reacts with itself by a Diels–Alder process to yield an adduct which decomposes to 3,3,8,8-tetramethyl-3,4,7,8-tetrahydroanthracene-1,6(2H,5H)-dione). When the substituted 1,4-naphthoquinone is unsymmetrical, a boron triacetate assisted Diels–Alder reaction gives a single regioisomer (e.g. X-ray investigations indicate that 8-hydroxy-3,3-dimethyl-3,4-dihydrobenz[a]anthracene-1,7,12(2H)-trione is the product from 5-hydroxy-1,4-naphthoquinone). An X-ray structural study of the Diels–Alder adduct in the above reaction confirms the operation of an endo cyclization.

scholarly journals Crystal structures and conformations of two Diels–Alder adduct derivatives: 1,8-bis(thiophen-2-yl)-14-oxatetracyclo[6.5.1.02,7.09,13]tetradeca-2(7),3,5-trien-10-one and 1,8-diphenyl-14-oxatetracyclo[6.5.1.02,7.09,13] tetradeca-2,4,6-trien-10-one

2015 ◽  
Vol 71 (2) ◽  
pp. 213-216
Author(s):  
S. Gopinath ◽  
P. Narayanan ◽  
K. Sethusankar ◽  
Meganathan Nandakumar ◽  
Arasambattu K. Mohanakrishnan
Keyword(s):  
Crystal Packing ◽  
Rotation Axis ◽  
Alder Reaction ◽  
Ring System ◽  
Diels Alder ◽  
Compound I ◽  
Diels Alder Reaction ◽  
Phenyl Rings ◽  
Axis Parallel ◽  
Alder Adduct

The title compounds, C21H16O2S2(I) and C25H20O2(II), are products of a tandem `pincer' Diels–Alder reaction consisting of [2 + 2] cycloadditions between benzo[c]furan and cyclopentanone. Each comprises a fused tetracyclic ring system containing two five-membered rings (inenvelopeconformations with the O atom as the flap) and six-membered rings (inboatconformations). In addition, two thiophene rings in (I) and two phenyl rings in (II) are attached to the tetracyclic ring system. The cyclopentanone ring adopts atwistedconformation in (I) and anenvelopeconformation in (II). In (I), the thiophene rings are positionally disordered over two sets of sites, with occupancy ratios of 0.901 (2):0.099 (2) and 0.666 (2):0.334 (2). In (II), the oxygen atom of the cyclopentanone ring is rotationally disordered over two sites with an occupancy ratio of 0.579 (4):0.421 (4). The molecular structure of (I) is stabilized by an intramolecular C—H...O hydrogen bond, which generates anS(7) ring motif. In the crystal, the molecules are linkedviaweak C—H...O hydrogen bonds, which generateR22(16) ring motifs in (I) andC(8) chains in (II). In both structures, the crystal packing also features C—H...π interactions. The crystal studied of compound (I) was twinned by non-merohedry. The twin component is related by the twin law [−1 0 0 −0.101 1 −0.484 0 0 −1] operated by a twofold rotation axis parallel to thebaxis. The structure of (I) was refined with a twin scale factor of 0.275 (2).

Diels-Alder reaction of pyrrole with dimethyl acetylenedicarboxylate

1978 ◽  
Vol 43 (19) ◽  
pp. 3727-3729 ◽  
Author(s):  
Chang Kiu Lee ◽  
Chi Sun Hahn ◽  
Wayland E. Noland
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Dimethyl Acetylenedicarboxylate ◽  
Diels Alder Reaction
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