C-Nucleosides and related compounds. VI. Carbocyclic analogues of C-nucleosides: synthesis and derivatives of some useful intermediates

1976 ◽  
Vol 54 (6) ◽  
pp. 849-860 ◽  
Author(s):  
George Just ◽  
Grant Reader ◽  
Bernadette Chalard-Faure
Keyword(s):  
Acrylic Acid ◽  
Wittig Reaction ◽  
Diels Alder ◽  
Reaction Products ◽  
Free Aldehyde ◽  
Derivatives Of ◽  
Related Compounds ◽  
Alder Adduct

The Diels–Alder adduct of cyclopentadiene and β-bromo acrylic acid 1 was converted to D,L-exo-6,7-(dihydroxy-di-O-isopropylidene)-2-hydroxy-3-oxabicyclo[3.2.1]octane (9) in an eight-step sequence and a 24% yield based on 1. Alternatively, the hemiacetal 9 was obtained in five steps and 22% yield from norbornadiene through the intermediate lactone 11. The thiosemicarbazone and semicarbazone of 9 were prepared. The synthesis of the free aldehyde 13 as well as that of the Wittig reaction products 12 and 19 are described.

C -Nucleosides and Related Compounds. IV. The Synthesis and Chemistry of D,L-2,5-Anhydroallose Derivatives

1975 ◽  
Vol 53 (1) ◽  
pp. 131-137 ◽  
Author(s):  
George Just ◽  
Alain Martel ◽  
Karl Grozinger ◽  
Mohabir Ramjeesingh
Keyword(s):  
Wittig Reaction ◽  
Diels Alder ◽  
Free Aldehyde ◽  
Related Compounds ◽  
Alder Adduct

Methyl β-nitroacrylate (1) reacted with furan to give the corresponding Diels–Alder adduct, which was converted to D,L-3,4-di-O-isopropylidene-2,5-anhydroallose (9) in a five-step sequence in 14% yield, based on 1. The conversion of 9 to its oxime, semicarbazone, and thiosemi-carbazone is described, as well as the synthesis of the free aldehyde 15, and of the Wittig reaction product 14.

Structures of derivatives of the Diels–Alder adduct 1,4,4a,5,8,8a,9a,10a-octahydro-1,4:5,8-dimethano-9,10-anthraquinone

1993 ◽  
Vol 49 (2) ◽  
pp. 303-307 ◽  
Author(s):  
G. Alex ◽  
S. Srinivasan ◽  
R. Bakthavatchalam ◽  
S. R. Ramadas ◽  
B. Varghese
Keyword(s):  
Diels Alder ◽  
Derivatives Of ◽  
Alder Adduct

C-Nucleosides and related compounds. XV. The synthesis of D,L-2′-epi-showdomycin and D,L-showdomycin

1980 ◽  
Vol 58 (19) ◽  
pp. 2024-2033 ◽  
Author(s):  
George Just ◽  
T. J. Liak ◽  
Mu-Ill Lim ◽  
Pierre Potvin ◽  
Youla S. Tsantrizos
Keyword(s):  
Diels Alder ◽  
Related Compounds ◽  
Alder Adduct

The conversion of the Diels–Alder adduct of methyl β-nitroacrylate with furan to the title compounds and to D,L-2,5-anhydroglucose derivatives is described.

scholarly journals Reaction of 2,5-Dimethylfuran with Ethyl Propiolate: The Chemistry of Ethyl 1,4-Dimethyl-7-oxabicyclo[2.2.1]hepta-2,5-diene-2-carboxylate

1975 ◽  
Vol 53 (10) ◽  
pp. 1496-1503 ◽  
Author(s):  
Archibald Wilson McCulloch ◽  
Alister Gavin McInnes
Keyword(s):  
Thermal Reaction ◽  
Diels Alder ◽  
Reaction Products ◽  
Minor Reaction ◽  
Alder Adduct

Thermal reaction of 2,5-dimethylfuran (1) and ethyl propiolate (2) affords the Diels–Alder adduct (3) and seven additional products, all of which are derived from 3. The major products, depending on the conditions, are the endo-exo 2:1 diadducts (4 and 5) and two nortricyclenes (8 and 10). The last two products arise by homo Diels–Alder type dimerization of 3 (to give 10) and subsequent Diels–Alder retrogression (to give 8). The minor reaction products include a third nortricyclene (9), isomeric with 8.

Synthesis of Some Naphthothiadiazolophanes. Derivatives of 4,10,14-Ethenylylidene-7H-[1,2,3]thiadiazolo[5,4-e]azacyclotridecine and 4,11,15-Ethenylylidene[1,2,3]thiadiazolo[5,4-f]azacyclotetradecine

1989 ◽  
Vol 42 (11) ◽  
pp. 1951 ◽  
Author(s):  
JB Bremner ◽  
W Jaturonrusmee
Keyword(s):  
Potassium Carbonate ◽  
Cyanogen Bromide ◽  
Diels Alder ◽  
Reaction Products ◽  
Analogous Structure ◽  
Derivatives Of

Reaction of 7,8-dimethoxy-1,2,4,5,1lb, 11c-hexahydrobenzo [de]pyrrolo[3,2,1-ij][1,2,3]thiadiazolo[4,5-g]quinoline (3a) and 8,9-dimethoxy-2,3,5,6,12b,12c-hexahydro-1H-[1,2,3]thiadiazolo-[5',4':3,4]naphtho[2,1,8-ijalquinoline (3b) with cyanogen bromide in the presence of potassium carbonate gave the naphthothiadiazolophanes 12,13-dimethoxy-5,6,8,9-tetrahydro-4,10,14- ethenylylidene-7H-[1,2,3]thiadiazolo[5,4-e]azacyclotridecine-7-carbonitrile (4a) and 13,14-di-methoxy-6,7,9,10-tetrahydro-4,11,15-ethenylylidene[1,2,3]thiadiazolo[5,4-f]azacyclotetradecine-8(5H)-carbonltrile (4b) in 39 and 89% yield respectively;7-(2-bromoethyl)-1,2-dimethoxy-5,6,6a,7-tetrahydro-4H-benzo[de][1,2,3]thiadiazolo[4,5-g]quinoline-6-car bonitrile (5a) was also obtained in 40% yield from the former reaction. Products of analogous structure resulted from (3a,b) when methyl chloroformate was used In place of cyanogen bromide. Attempted Diels-Alder reactions of (4b,c) with some powerful dienophiles were unsuccessful.

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