Diels-Alder Reactions of Vinyl Derivatives of [1]Benzothieno[3,2-b]furan

1999 ◽  
Vol 64 (2) ◽  
pp. 389-407 ◽  
Author(s):  
Pavel Pihera ◽  
Hana Dvořáková ◽  
Jiří Svoboda
Keyword(s):  
Double Bond ◽  
Carboxylic Acid ◽  
Dicarboxylic Acid ◽  
Diels Alder ◽  
Dimethyl Acetylenedicarboxylate ◽  
Carboxylic Group ◽  
Methyl Propiolate ◽  
Vinyl Derivatives ◽  
Hydrolysis Of ◽  
Derivatives Of

2-Vinyl- (2) and 3-vinyl[1]benzothieno[3,2-b]furan (3) react with dimethyl acetylenedicarboxylate, methyl propiolate, maleic anhydride, or acrylonitrile endo-selectively as dienes to afford new [1]benzothieno[3,2-b][1]benzofuran derivatives 7-20. cis-Anhydrides 13 and 18 were transformed into dimethyl esters 21 and 22, respectively. It was shown that the base-catalyzed hydrolysis of 13 and 18 is accompanied by rearrangement of double bond in 13 and cis/trans isomerization of carboxylic group. Diesters 21 and 22, and nitriles 20 and 24 were aromatized by treatment with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. Selective monodecarboxylation of [1]benzothieno[3,2-b][1]benzofuran-8,9-dicarboxylic acid (26) and [1]benzothieno[3,2-b][1]benzofuran-6,7-dicarboxylic acid (27) afforded [1]benzothieno[3,2-b][1]benzofuran-8-carboxylic acid (28) and [1]benzothieno[3,2-b][1]benzofuran-7-carboxylic acid (29), respectively.

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.

Isocarbostyrils. II. The Conversion of 2-Methyl-4-acyl-5-nitroisocarbostyrils to 2-Substituted Indole-4-carboxylic Acids

1971 ◽  
Vol 49 (17) ◽  
pp. 2797-2802 ◽  
Author(s):  
D. E. Horning ◽  
G. Lacasse ◽  
J. M. Muchowski
Keyword(s):  
Sulfuric Acid ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Alkaline Hydrolysis ◽  
Mannich Reaction ◽  
Reductive Cyclization ◽  
Acid Catalyzed ◽  
Acid Anhydrides ◽  
Hydrolysis Of ◽  
Derivatives Of

The sulfuric acid catalyzed acylation of 2-methyl-5-nitroisocarbostyril with carboxylic acid anhydrides gave the corresponding 4-acylated derivatives 3, which underwent reductive cyclization to 2-substituted derivatives of 4-methyl-1,3,4,5-tetrahydropyrrolo[4.3.2.de]isoquinolin-5-one (4). Alkaline hydrolysis of the six-membered lactam in 4 was accompanied by a retro-Mannich reaction to produce 2-substituted indole-4-carboxylic acids in about 40 % overall yield from 3.

The reaction of steroid 2,4-dienes with acetylenes

1976 ◽  
Vol 54 (22) ◽  
pp. 3508-3516 ◽  
Author(s):  
Peter Yates ◽  
Françoise M. Walliser
Keyword(s):  
Diels Alder ◽  
The Other ◽  
Dimethyl Acetylenedicarboxylate ◽  
Methyl Propiolate ◽  
Lower Temperature

Reaction of 2,4-cholestadiene, 2,4-androstadien-17-one, or 3-trimethylsiloxy-2,4-cholestadiene with dimethyl acetylenedicarboxylate or methyl propiolate in boiling xylene results in the cleavage of rings A and B and the formation of 4-(2-arylethyl)-5-isopropenyl-7a-methyltetrahydroindane derivatives. They are considered to be formed via Diels–Alder addition of the acetylene to the steroid diene followed by a retro-Diels–Alder cleavage of the resulting bicyclo[2.2.2]octadiene system. Attempts to isolate the Diels–Alder adducts by carrying out the additions at lower temperature were unsuccessful, since no reaction occurred. However, when 2,4-androstadien-17-one was treated with dicyanoacetylene in boiling benzene, it was possible to isolate a mixture of two stereoisomeric Diels–Alder adducts containing the bicyclo[2.2.2]octadiene system in ring A; this was converted in boiling xylene to a retro-Diels–Alder product analogous to the products obtained with the other acetylenic dienophiles.

ChemInform Abstract: KINETICS OF THE ACID HYDROLYSIS OF VINYL DERIVATIVES OF BENZIMIDAZOLE-2-THIONE, BENZOXAZOL-2-ONE AND -2-THIONE

1983 ◽  
Vol 14 (17) ◽  
Author(s):  
L. I. SVYATKINA ◽  
N. D. ABRAMOVA ◽  
L. L. DMITRIEVA ◽  
B. V. TRZHTSINSKAYA ◽  
G. G. SKVORTSOVA
Keyword(s):  
Acid Hydrolysis ◽  
Vinyl Derivatives ◽  
Kinetics Of ◽  
Hydrolysis Of ◽  
Derivatives Of

ChemInform Abstract: Diels-Alder Reactions of Vinyl Derivatives of [1]Benzothieno[3,2-b]furan.

ChemInform ◽  
2010 ◽  
Vol 30 (32) ◽  
pp. no-no
Author(s):  
Pavel Pihera ◽  
Hana Dvorakova ◽  
Jiri Svoboda
Keyword(s):  
Diels Alder ◽  
Vinyl Derivatives ◽  
Derivatives Of

ChemInform Abstract: DIELS-ALDER REACTIONS OF VINYL DERIVATIVES OF FIVE-MEMBERED MONOHETEROCYCLIC COMPOUNDS

1983 ◽  
Vol 14 (51) ◽  
Author(s):  
W. E. NOLAND ◽  
C. K. LEE ◽  
S. K. BAE ◽  
B. Y. CHUNG ◽  
C. S. HAHN ◽  
...  
Keyword(s):  
Diels Alder ◽  
Vinyl Derivatives ◽  
Derivatives Of

Diels-Alder reactions of vinyl derivatives of five-membered monoheterocyclic compounds

1983 ◽  
Vol 48 (15) ◽  
pp. 2488-2491 ◽  
Author(s):  
Wayland E. Noland ◽  
Chang Kiu Lee ◽  
Sun Kun Bae ◽  
Bong Yul Chung ◽  
Chi Sun Hahn ◽  
...  
Keyword(s):  
Diels Alder ◽  
Vinyl Derivatives ◽  
Derivatives Of

The stereochemistry and regiochemistry of the Diels–Alder reactions of 6-acetoxy-2,6-dimethyl-2,4-cyclohexadienone

1981 ◽  
Vol 59 (16) ◽  
pp. 2510-2517 ◽  
Author(s):  
Hillar Auksi ◽  
Peter Yates
Keyword(s):  
Carboxylic Acid ◽  
Maleic Anhydride ◽  
Dicarboxylic Acid ◽  
Van Der Waals ◽  
Closed Shell ◽  
Diels Alder ◽  
Acid Anhydride ◽  
Propiolic Acid ◽  
High Stereoselectivity

6-Acetoxy-2,6-dimethyl-2,4-cyclohexadienone (1) and maleic anhydride in boiling benzene give a single adduct, exo-5-acetoxy-l,5-dimethyl-6-oxobicyclo[2.2.2]oct-7-ene-endo-2,3-dicarboxylic acid anhydride (2). With propiolic acid 1 gives exo-5-hydroxy-l,5-dimethyl-6-oxobicyclo[2.2.2]octa-2,7-diene-2-carboxylic acid (15). The high stereoselectivity and regioselectivity of these reactions is interpretable in terms of orbital overlap, closed-shell repulsion, steric, and van der Waals – London effects.

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