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

Diels-Alder Reaction of Enaminodithiocarboxylate Derivatives with Dimethyl Acetylenedicarboxylate

Heterocycles ◽  
1975 ◽  
Vol 3 (1) ◽  
pp. 85 ◽  
Author(s):  
Goro Kobayashi ◽  
Kzumichi Mizuyama ◽  
Yoshinori Miyake ◽  
Yoshinori Tominaga ◽  
Yoshiro Matsuda
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Dimethyl Acetylenedicarboxylate ◽  
Diels Alder Reaction

Vinylindenes and Some Heteroanalogs in the Diels-Alder Reaction. X. Dibenzofurans From 3-Vinylbenzofurans

1991 ◽  
Vol 44 (8) ◽  
pp. 1085 ◽  
Author(s):  
JR Pearson ◽  
QN Porter
Keyword(s):  
Maleic Anhydride ◽  
Alder Reaction ◽  
Diels Alder ◽  
Dimethyl Acetylenedicarboxylate ◽  
Diels Alder Reaction

3-Vinylbenzofuran, 3-isopropenylbenzofuran and 2-methyl-3-vinylbenzofuran give normal [4π+2π] adducts with ethenetetracarbonitrile, accompanied, in the case of the last named diene, by the isomeric cyclobutane. Normal adducts also result from these dienes and 4-phenyl-1,2,4-triazoline-3,5-dione, and from 3-vinylbenzofuran and both maleic anhydride and N- phenylmaleimide. 3-Vinylbenzofuran gives the rearranged adduct dimethyl 1,2-dihydrodibenzofuran-3,4-dicarboxylate with dimethyl acetylenedicarboxylate.

Vinylindenes and some heteroanalogues in the Diels-Alder reaction. II. Substituted fluorenes from 3-vinylindenes

1977 ◽  
Vol 30 (5) ◽  
pp. 1061 ◽  
Author(s):  
R Bergamasco ◽  
QN Porter
Keyword(s):  
Mass Spectrometry ◽  
Maleic Anhydride ◽  
Alder Reaction ◽  
Diels Alder ◽  
Dimethyl Acetylenedicarboxylate ◽  
Diels Alder Reaction

3-Vinylindene, 2-methyl-3-vinylindene and 3-isopropenylindene give normal, photostable adducts with ethenetetracarbonitrile by a Diels- Alder process. The first diene gives adducts with maleic anhydride, N- phenylmaleimide and dimethyl acetylenedicarboxylate. Where there is stereochemical ambiguity the adducts are shown by mass spectrometry to be exclusively endo. Two heterocyclic analogues are formed from 3- vinylindene with p-toluenesulphonyl cyanide and N-sulphinyl-p- toluenesulphonamide.

Influence of Lewis acids on the Diels–Alder reaction. III. Rearrangement of dimethyl N-carbomethoxy-7-azabicyclo[2.2.1]2,5-heptadiene-2,3-dicarboxylate adducts to dimethyl N-carbomethoxy-3-aminophthalates

1970 ◽  
Vol 48 (9) ◽  
pp. 1472-1474 ◽  
Author(s):  
R. C. Bansal ◽  
A. W. McCulloch ◽  
A. G. McInnes
Keyword(s):  
Aluminum Chloride ◽  
Lewis Acids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Prolonged Treatment ◽  
Dimethyl Acetylenedicarboxylate ◽  
Diels Alder Reaction ◽  
Convenient Route

Aluminum chloride accelerates the Diels–Alder reactions of 2- or 2,5-substituted N-carbomethoxypyrroles with dimethyl acetylenedicarboxylate, and also catalyzes rearrangement of the N-carbomethoxy-7-azanorbornadiene adducts to 6- and 4,6-substituted dimethyl N-carbomethoxy-3-aminophthalates. Aromatization of the corresponding adduct of N-carbomethoxypyrrole only occurs on prolonged treatment with BF3. The procedure promises to be a convenient route for the synthesis of polysubstituted anilines.

scholarly journals Two-Carbon Ring Enlargement of Five-, Six-, and Seven-Membered 1-Aza-2-vinylcycloalk-2-enes with Dimethyl Acetylenedicarboxylate and Subsequent Thermal Isomerization Reactions

2006 ◽  
Vol 61 (4) ◽  
pp. 385-395 ◽  
Author(s):  
Gerhard Maas ◽  
Robert Reinhard ◽  
Hans-Georg Herz
Keyword(s):  
Elevated Temperatures ◽  
Alder Reaction ◽  
Thermal Isomerization ◽  
Diels Alder ◽  
Dimethyl Acetylenedicarboxylate ◽  
X Ray ◽  
Ring Enlargement ◽  
Diels Alder Reaction ◽  
Carbon Ring ◽  
Electrocyclic Reaction

2-Aminodienes, in which the enamine function is incorporated in a five-, six-, or seven-membered ring, react with dimethyl acetylenedicarboxylate in a sequence of [2+2] cycloaddition and electrocyclic ring-opening to form the two-carbon ring expanded unsaturated heterocycles, i.e., 3,4- dicarboxylate substituted 6,7-dihydro-1H-azepines 3, 8 and 21, 1,6,7,8-tetrahydroazocines 22, and 6,7,8,9-tetrahydro-1H-azonines 13. Similarly, 2-[(2-thienyl)ethynyl]-4,5,6,7-tetrahydro-1H-azepine 9 is converted into 2-[(2-thienyl)ethynyl]-6,7,8,9-1H-azonine-3,4-dicarboxylate 10 which was characterized by X-ray structure determination. The eight- and nine-membered azaheterocycles 22 and 13, which have not been isolated, undergo thermal isomerization at elevated temperatures. Thus, ring contraction by a 6π-electrocyclic reaction takes place for N-methyl substituted azonine 13, while the N-allyl moiety of azocines 22 engages in an intramolecular Diels-Alder reaction or a 1,7- electrocyclization reaction

Sign in / Sign up

Export Citation Format

Share Document