The Diels-Alder reaction of some styrenes and 2,2-dimethylchromenes with acetylenic esters

1969 ◽  
Vol 22 (8) ◽  
pp. 1721 ◽  
Author(s):  
JA Diment ◽  
E Ritchie ◽  
WC Taylor
Keyword(s):  
Linear Structure ◽  
Alder Reaction ◽  
Diels Alder ◽  
Dimethyl Acetylenedicarboxylate ◽  
Acetylenic Esters ◽  
Methyl Propiolate ◽  
Diels Alder Reaction ◽  
Derivatives Of

Examples of the Diels-Alder reaction between some derivatives of styrene and of 2,2-dimethylchromene and dimethyl acetylenedicarboxylate and methyl propiolate, leading ultimately to fully aromatic derivatives, are described. Yields are generally low and the synthesis has limited utility. However, the n.m.r, spectrum of the product from acronycine dimethyl acetylenedicarboxylate is such as to establish the angular rather than the linear structure for acronycine.

Reaction of 2-[(E)-styryl]Quinazolin-4(3H)-one with Acetylenic Esters: Formation of Unexpected N-3 Alkenylation Products

2005 ◽  
Vol 2005 (7) ◽  
pp. 429-431 ◽  
Author(s):  
Tapasi Chatterjee ◽  
Subhagata Chattopadhyay ◽  
Ranjan Mukhopadhyay ◽  
Basudeb Achari ◽  
Santu Chakraborty ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Alder Reaction ◽  
Diels Alder ◽  
Dimethyl Acetylenedicarboxylate ◽  
Acetylenic Esters ◽  
X Ray ◽  
Methyl Propiolate ◽  
Diels Alder Reaction ◽  
Centrosymmetric Dimers

Attempted hetero Diels–Alder reaction with 2-[(E)-styryl]quinazolin-4(3H)-one (1) and dimethyl acetylenedicarboxylate (2) resulted in unexpected N-3 alkenylation products, 2-[(E)-styryl]-3-[(Z)-1,2-bis(methoxycarbonyl)vinyl]quinazolin-4(3H)-one (4a) and 3-[(E)-1,2-bis(methoxycarbonyl) vinyl] 2-[(E)-styryl]-quinazolin-4(3H)-one (4b) in low yield. Treating 1 and 2-methylquinazolin-4(3H)-one (9) with methyl propiolate (7) also furnished N-3 alkenylation products in low yield. The structure of 4b has been established by X-ray analysis. The molecules of 4b are linked by intermolecular C-H. … N hydrogen bonds into centrosymmetric dimers forming R22 (12) rings.

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

Cycloadditionen, XXII [1]. Synthese und thermische Reaktion von S-(Alkyl/Aryl)- 2.3-butadienthiosäure-estern / Cycloadditions, XXII [1]. Synthesis and Thermal Reaction of S-(Alkyl/Aryl)-2,3-butadienethioates

1994 ◽  
Vol 49 (4) ◽  
pp. 542-550 ◽  
Author(s):  
Gerhard Himbert ◽  
Dieter Fink
Keyword(s):  
Alder Reaction ◽  
Thermal Reaction ◽  
Diels Alder ◽  
Alkyl Aryl ◽  
Diels Alder Reaction ◽  
Ester Moiety ◽  
Derivatives Of

While the S-alkyl- or S-phenyl-2,3-butadienethioates 4 a-c are synthesized via the usual “Wittig ylide way”, the corresponding 2-methyl-2,3-butadienethioates 9 a-d and the 2-methyl-4.4-diphenyl-2,3-butadienethioates 9 e,f are obtained by condensation of the allenic acids 7 a,b with the thiols and thiophenols 8 in the presence of dicyclohexylcarbodiimide (DCC) and a catalytic am ount of 4-dimethylaminopyridine (DMAP). In contrast to N- or O-phenyl 2,3- butadienamides or -esters, resp., the phenyl derivatives of 4 and 9 do not undergo the intram olecular Diels-Alder reaction, but by heating, all representatives of 4 only decompose, while 9 a-d and 9 e,f rearrange to 3-alkyl(aryl)thio-2-cyclobuten-1-ones 12a-d and to 3-arylthio- 1-naphthols 14a, b, resp. Heating of the cyclobutenone 12d in the presence of N-methylaniline furnishes the 2-butenanilide 16. On reacting 1-phenylthio-1-propyne 17 with diphenylketene 18, the diphenylacetate 19 is isolated, where the naphthol derivative 14a represents the ester moiety.

An examination of VANOL, VAPOL, and VAPOL derivatives as ligands for asymmetric catalytic Diels–Alder reactions

2006 ◽  
Vol 84 (10) ◽  
pp. 1487-1503 ◽  
Author(s):  
Douglas P Heller ◽  
Daniel R Goldberg ◽  
Hongqiao Wu ◽  
William D Wulff
Keyword(s):  
Asymmetric Catalysis ◽  
Methyl Acrylate ◽  
Lewis Acids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Asymmetric Catalytic ◽  
Diels Alder Reaction ◽  
Positive Cooperativity ◽  
Derivatives Of ◽  
Methyl Phenyl

Several derivatives of the vaulted biaryl ligand VAPOL were prepared and evaluated as chiral ligands for aluminum Lewis acids in the catalytic asymmetric Diels–Alder reactions of methyl acrylate and methacrolein with cyclopentadiene. The substituents on VAPOL were introduced into the 6- and 6′-positions in an effort to further extend the chiral pocket of the major groove, which contains the phenol functions at the 4- and 4′-positions. The set of four new ligands that have been prepared have the following groups introduced into the 6- and 6′-positions of VAPOL: bromide, methyl, phenyl and 3,5-di-t-butylphenyl. All of these ligands give lower asymmetric inductions than the unsubstituted VAPOL for the Diels–Alder reactions of both methyl acrylate and methacrolein. The positive cooperativity of added carbonyl compounds on the autoinduction in the Diels–Alder reaction of methyl acrylate and cyclopentadiene were also investigated with the VANOL and VAPOL ligands as well as the 6,6′-dibromo and 6,6′-diphenyl derivatives of VAPOL. Only the reaction with VAPOL showed any significant positive cooperativity. The reaction with VANOL was sluggish at –78 °C, but at higher temperatures, the reaction did exhibit positive cooperativity that was similar to that of VAPOL. Finally, no positive cooperativity was observed with the VAPOL ligand for the reaction of methacrolein and cyclopentadiene.Key words: Diels–Alder, asymmetric catalysis, vaulted biaryl ligands, VANOL, VAPOL.

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.

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