Photochemical synthesis of 8H-Benzo[g]- 1,3-benzodioxolo[6,5,4-de]quinolin-8-one (Liriodenine) via 7-Methyl-6,7-dihydro-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]-quinoline

1983 ◽  
Vol 36 (5) ◽  
pp. 1061 ◽  
Author(s):  
S Nimgirawath ◽  
WC Taylor
Keyword(s):  
Lead Tetraacetate ◽  
Aluminium Chloride ◽  
Photochemical Synthesis ◽  
Lithium Aluminium Hydride ◽  
Methyl Derivative ◽  
Lithium Aluminium ◽  
Moderate Yield

Irradiation of ethyl (Z)-1-(2-bromobenzylidene)-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (4) afforded ethyl 6,7-dihydro-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline-7-carboxylate (5), the reduction of which with lithium aluminium hydride-aluminium chloride gave the 7-methyl derivative (6). Oxidation of (6) with lead tetraacetate afforded liriodenine (8H-benzo[g]-1,3-benzodioxolo[6,5,4-delquinolin-8-one)(1) in moderate yield.

HYDROGENOLYSIS BY LITHIUM ALUMINIUM HYDRIDE – ALUMINIUM CHLORIDE OF ETHER SOLUTIONS OF CAMPHOR ETHYLENE KETAL AND NORCAMPHOR ETHYLENE KETAL

1966 ◽  
Vol 44 (13) ◽  
pp. 1547-1550 ◽  
Author(s):  
W. W. Zajac Jr. ◽  
B. Rhee ◽  
R. K. Brown
Keyword(s):  
Reductive Cleavage ◽  
Aluminium Chloride ◽  
Lithium Aluminium Hydride ◽  
Similar Reduction ◽  
Lithium Aluminium

The lithium aluminium hydride – aluminium chloride reductive cleavage of norcamphor ethylene ketal yields 2-(2-endo-norbornyloxy)ethanol in ≥98% yield, whereas the similar reduction of camphor ethylene ketal gives 2-(2-isobornyloxy)ethanol in 78% yield and 2-(2-bornyloxy)ethanol in 22% yield. These are the products arising from steric approach control.

Lithium aluminium hydride-aluminium chloride reduction of steroidal cyclic acetals

1971 ◽  
Vol 24 (1) ◽  
pp. 143 ◽  
Author(s):  
MS Ahmad ◽  
SC Logani
Keyword(s):  
Spectral Properties ◽  
Aluminium Chloride ◽  
Chemical Transformations ◽  
Lithium Aluminium Hydride ◽  
Glycol Ethers ◽  
Cyclic Acetals ◽  
Lithium Aluminium

Lithium aluminium hydride-aluminium chloride (1 : 1, AlH2Cl) reduction of 3,3-ethylenedioxycholest-5-ene (5), 3,3-ethylenedioxy-5α-oholestane (7), 6,6-ethyl-enedioxy-5α-cholestane (7), and 3,3-(1?- methylethylenedioxy)cholest-5-en (8a), gave the glycol ethers (9), (17), (21a), and (24), respectively. The structures of the ethers (9), (17), (21a), and (24) have been established by their spectral properties and chemical transformations. A mechanism of the hydrogenolysis is presented.

Regulators of cell division in plant tissues. VII. The synthesis of zeatin and related 6-substituted purines

1969 ◽  
Vol 22 (1) ◽  
pp. 205 ◽  
Author(s):  
DS Letham ◽  
RE Mitchell ◽  
T Cebalo ◽  
DW Stanton
Keyword(s):  
Zea Mays ◽  
Cell Division ◽  
Acid Hydrolysis ◽  
Sodium Borohydride ◽  
Aluminium Chloride ◽  
Plant Tissues ◽  
Lithium Aluminium Hydride ◽  
Lithium Aluminium

6-(4-Hydroxy-3-methylbut-trans-2-enylamino)purine (zeatin), a cytokinin isolated from Zea mays, has been synthesized by a new route. β- Methylcrotononitrile was brominated with N-bromosuccinimide yielding γ- bromo-β-methylcrotononitrile, from which trans-γ-acetoxy-β- methylcrotononitrile was prepared. The alcohol derived from this acetate was converted into trans-β-methyl-γ-(tetrahydropyran-2- yloxy)crotononitrile. Reduction and acid hydrolysis gave 4-amino-2- methylbut-trans-2-en-1-ol which was made to react with 6-chloropurine to yield zeatin. ��� Several γ-alkoxy-β-methylcrotononitriles were prepared and reduced by aluminium chloride-lithium aluminium hydride to the corresponding unsaturated amines. Saturated nitrile formation also occurred in these reductions. The amines prepared were condensed with 6-chloropurine to yield a series of O-alkylzeatins. A number of other zeatin analogues were also synthesized. Two 6-methoxyalkylamino-purines were cleaved by sodium borohydride in the presence of iodine to 6-hydroxy- alkylaminopurines.

scholarly journals Reduction of Chalcones by Complex Metal Hydrides. III. Chalcone and Chain-deuterated Chalcones with Lithium Aluminium Hydride-Aluminium Chloride.

1969 ◽  
Vol 23 ◽  
pp. 2409-2413 ◽  
Author(s):  
Tapio Hase ◽  
Boris Holm ◽  
Johannes Thomsen ◽  
Károly Kovács ◽  
Alf A. Lindberg ◽  
...  
Keyword(s):  
Metal Hydrides ◽  
Aluminium Chloride ◽  
Lithium Aluminium Hydride ◽  
Complex Metal ◽  
Lithium Aluminium

scholarly journals Reduction of Chalcones by Complex Metal Hydrides. II. 4- and 4'-Methoxychalcone with Lithium Aluminium Hydride-Aluminium Chloride.

1969 ◽  
Vol 23 ◽  
pp. 2403-2408 ◽  
Author(s):  
Tapio Hase ◽  
Olav Smidsrød ◽  
Arne Haug ◽  
Terence Painter ◽  
J. Rydberg ◽  
...  
Keyword(s):  
Metal Hydrides ◽  
Aluminium Chloride ◽  
Lithium Aluminium Hydride ◽  
Complex Metal ◽  
Lithium Aluminium
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