Cyanogen-Bromide-Mediated and Methyl-Chloroformate-Mediated Synthesis of Some [3]Benzazonino[8,7,6-abc]Carbazole, [3]Benzazecino[9,8,7-abc]Carbazole, Naphth[1,8,7-def]Azonine and Naphth[1,8,7-def]Azecine Derivatives

1986 ◽  
Vol 39 (1) ◽  
pp. 1 ◽  
Author(s):  
JB Bremner ◽  
KN Winzenberg
Keyword(s):  
Magnesium Oxide ◽  
Potassium Carbonate ◽  
Cyanogen Bromide ◽  
Reaction Products ◽  
Analogous Structure ◽  
Lithium Tetrahydroaluminate ◽  
Elimination Reactions

Reaction of 7,8-dimethoxy-1,4,5,9,13c,13d-hexahydro-2H-indolo [3′,2′:4,5] indolo [1,7,6-aji] isoquinoline (4a) and 8,9-dimethoxy- 1,2,3,5,6,10,14c,14d-octahydro-indolo[3′,2′:3,4] naphtho [2,1,8-ija] quinolizine (4b) with cyanogen bromide in the presence of potassium carbonate afforded the elimination products 7,8-dimethoxy-1,2,3,4,5,9- hexahydro [3] benzazonino [8,7,6-abc]carbazole-3-carbonitrile (5a) and 8,9-dimethoxy-2,3,4,5,6,10-hexahydro-1H-[3] benzazecino [9,8,7-abc]carbazole-4-carbonitrile (5b) in 4% and 88% yield respectively; 7- (2-bromo)ethyl-1,2-dimethoxy-4,5,6,6a,7,12-hexahydroisoquino[8,1-ab ]carbazole-6-carbonitrile (6a) was also isolated in 20% yield from the former reaction. Products of analogous structure were also obtained from (4a,b) when methyl chloroformate was used in place of cyanogen bromide. Reaction of (4b) with cyanogen bromide in the presence of water and magnesium oxide afforded the solvolysis product 14d-hydroxy-8,9-dimethoxy-2,3,4,5,6,10,14d,14d-octahydro-1H-[3] benzazecino [9,8,7- abc ]carbazole-4-carbonitrile (8b) together with (5b). Similarly application of this reaction to 8,9-dimethoxy-2,3,5,6,11a,11b-hexahydro-1H-naphtho[2,1,8-ija] quinolizine (1b) afforded both the corresponding solvolysis and elimination products; (4a) and 7,8- dimethoxy-1,2,4,5,10a,10b-hexahydronaphtho[1,8,7-ghi] indolizine (1a), however, gave only solvolysis products. Solvolysis and elimination products were also isolated when (1b) and (4b) were subjected to cyanogen -bromide-mediated methanolysis reactions. Acid-catalysed elimination reactions of the alcohol solvolysis products are described along with reaction of some of the elimination products with lithium tetrahydroaluminate.

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.

Synthesis of 1H-[1]Benzothieno[3,2-d]azonine and [1]Benzothieno[3,2-d]azecine Derivatives

1985 ◽  
Vol 38 (5) ◽  
pp. 765 ◽  
Author(s):  
EJ Browne
Keyword(s):  
Aqueous Medium ◽  
Magnesium Oxide ◽  
Cyanogen Bromide ◽  
Functional Group ◽  
Ring System ◽  
Cyclic Ketones ◽  
Phenyl Derivative ◽  
E And Z Isomers ◽  
Derivatives Of ◽  
Medium Ring

Derivatives of two new [1] benzothieno medium-ring heterocyclic systems have been prepared by ring degradation using cyanogen bromide-induced solvolysis of tetracyclic precursors. Reaction of a hexahydro -[1] benzothieno [3,2-g] indolizine (4a) and a hexahydro-2H-[1] benzo-thieno [2,3-a] quinolizine (4b) with cyanogen bromide and magnesium oxide under solvolytic conditions yielded the hexahydro-1H-[1] benzothieno [3,2-d] azonines (5a) and (6a) and the octahydro -[1] benzothieno [3,2-d] azecines (5b) and (6b), respectively. Functional group interconversions of these medium-ring systems are described, including oxidations to the cyclic ketones (7) and (9). The 11b-phenyl derivative (13) of (4a) reacted under similar conditions to give both solvolysis (14) and (16) and elimination (15) medium-ring products, the ratios depending on the solvent. By contrast the analogous 9a-phenylthienoindolizine derivative (17) under these conditions gave only the medium-ring elimination product (18) in aqueous medium, and only the equivalent solvolysis product in methanol. Both the thieno and [1] benzothienoazonine elimination products (18) and (15) appear to be mixtures of E and Z isomers. The [1] benzothieno [3,2-g] indolizine bases (4a) and (13) are the first reported examples of this ring system.

Synthesis of 4H-Thieno[2,3-d]azonine and Thieno[2,3-d]azecine derivatives

1984 ◽  
Vol 37 (2) ◽  
pp. 367 ◽  
Author(s):  
EJ Browne
Keyword(s):  
Magnesium Oxide ◽  
Cyanogen Bromide ◽  
Functional Group ◽  
Cyclic Ketones ◽  
Ring Systems ◽  
Phenyl Derivative ◽  
Derivatives Of ◽  
Medium Ring

Derivatives of two new thieno medium-ring heterocyclic systems have been prepared by ring degradation using cyanogen bromide-induced solvolysis of tricyclic bases. Reaction of a hexahydrothieno[2,3-glindolizine (4a) and a hexahydro-7H-thieno[3,2-a]quinolizine (4b) with cyanogen bromide and magnesium oxide under solvolytic conditions yielded derivatives of hexahydro-4H-thieno[2,3-d]azonine (5a) (6a) and octahydrothieno[2,3-d]azecine (5b) (6b), respectively. Functional group interconversions of these medium-ring systems are described, including oxidations to cyclic ketones. The 9a-phenyl derivative of (4a) reacted similarly. By contrast 10b-phenyl derivatives (10a,b) of a hexahydropyrrolo[2,1-a]isoquinoline reacted under these conditions to give medium-ring elimination products, derivatives of tetrahydro-1H-3-benzazonines.

Study on the Promoting Effect of Additive on the Calcium-Based Sulfur-Fixing Agent

2013 ◽  
Vol 773 ◽  
pp. 634-638 ◽  
Author(s):  
Ying Zhu ◽  
Chuan Liu ◽  
Qiao Wen Yang ◽  
Peng Fei Li ◽  
Yong Jun Sun ◽  
...  
Keyword(s):  
Fly Ash ◽  
Magnesium Oxide ◽  
Potassium Carbonate ◽  
Red Mud ◽  
Orthogonal Experiment ◽  
Mass Ratio ◽  
Promoting Effect ◽  
Fixation Capacity ◽  
Sulfur Fixation ◽  
Shell Powder

Based on the removal of SO2 as the research background, this paper focuses on the research of mono-component experiment and orthogonal experiment of compound sulfur-fixing agent composed of shell powder and red mud (at the mass ratio of 8:2) at the temperature of 1000°C and Ca/S was 2.0, by adding manganese dioxide, fly ash, magnesium oxide and potassium carbonate as the sulfur-fixing additive. The experimental results showed that the sulfur fixation capacity of desulfurizer is increased to different extents and the optimal ratio to additive is obtained after addition of the additive.

Sol-gel-derived Magnesium Oxide Precursor for Thin-film Fabrication

2000 ◽  
Vol 15 (4) ◽  
pp. 842-845 ◽  
Author(s):  
Hyungsoo Choi ◽  
Soontaik Hwang
Keyword(s):  
Magnesium Oxide ◽  
Sol Gel ◽  
Acid Catalyst ◽  
Heat Treating ◽  
Magnesium Acetate ◽  
Reaction Products ◽  
Differential Thermal Analysis Peak ◽  
Thin Film Fabrication ◽  
Surface Oxides ◽  
Gel Processing

Magnesium oxide (MgO) precursors were prepared by the sol-gel method using magnesium acetate. The reaction products and intermediates obtained during the sol-gel processing of magnesium acetate under various conditions were analyzed thermally and spectroscopically. No organic groups were detected by infrared spectroscopy after heat treating the reaction products at 400 °C. A large exothermic differential thermal analysis peak below 400 °C demonstrated the oxidation of organic moieties in each product. It was found that the presence of an acid catalyst was crucial during the sol-gel processing of magnesium acetate to produce sols suitable for depositing MgO films. The MgO films fabricated on Si(111) substrates using the precursor sol showed (200) orientation regardless of the presence of surface oxides on the substrates.

Synthesis of Benzo[D]Thieno[2,3-G]Azecine and Benzo[D][1]Benzothieno[2,3-G]Azecine Derivatives

1986 ◽  
Vol 39 (5) ◽  
pp. 783 ◽  
Author(s):  
EJ Browne
Keyword(s):  
Magnesium Oxide ◽  
Cyanogen Bromide ◽  
Functional Group ◽  
Cyclic Ketones ◽  
Ring Systems ◽  
Derivatives Of ◽  
Medium Ring

Derivatives of two new diannulated azecine systems have been prepared by ring degradation of precursor bases with cyanogen -bromide-induced solvolysis. Reaction of a tetrahydro-5H-benzo[h] thieno [2,3,-a] quinolizine (5a) and a tetrahydro-7H-benzo[h][1] benzothieno [2,3-a] quinolizine (5b) with cyanogen bromide and magnesium oxide under solvolytic conditions yielded derivatives of a hexahydrobenzo [d] thieno [2,3-g] azecine (6a) and a hexahydrobenzo [d][1] benzothieno [2,3-g] azecine (6b), respectively. Functional group interconversions of these medium-ring systems were performed, including oxidations to cyclic ketones. The 5H-benzo[h] thieno [2,3-a] quinolizine and 7H-benzo[h] [l] benzothieno [2,3-a] quinolizine bases (5a) and (5b) are the first reported examples of these ring systems.

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