Gibberellins and related compounds

Conclusions A study was made of the photochemical aromatization of the 2-keto derivative of gibberellic acid in various solvents. Unusual fragmentation of the B ring, with the formation of the seco-structure, was observed when the reaction was run in benzyl alcohol.Deceased.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2037–2040, September, 1971.     

Gibberellins and related substances

Conclusions 1. A study of the gibberellin-like substances of the leaves of tobaccoN. tabacum has shown that the latter contains gibberellin A₃ and possibly A₆ in the free state.The amount of GA₃ in the leaves of this plant is approximately 0.2–2 µg/kg.2. In addition, tobacco leaves contain neutral gibberellin-like substances in the bound form which are liberated on hydrolysis.Khimiya Prirodnykh Soedinenii, Vol. 5, No. 4, pp. 296–304, 1969     

Gibberellins and related substances

Conclusions The principles of the reduction of 2-keto-derivatives of gibberellic acid by complex metal hydrides were studied, and the synthesis of the epimer of gibberellic acids and its ester was carried out.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1805–1809, August, 1969.The authors would like to thank V. I. Zaretskii and I. B. Papernaya for taking the mass spectra and discussing the results and A. V. Kessenikh for the NMR spectra.     

Gibberellins and related substances

Chemistry of Natural Compounds - 1. A study of the gibberellin-like substances of the leaves of tobaccoN. tabacum has shown that the latter contains gibberellin A3 and possibly A6 in the free...     

Gibberellins and substances related to them

Conclusions 1. The neutral metabolites elaborated byFusarium moniliforme (strain F-6) in various medi have been chromatographed and six known diterpenoids biogenetically related to the gibberellins have been identified.2. The influence of the rate of consumption of the source of C during fermentation and its chemical nature on the course of the biosynthesis of the gibberellins have been noted.3. Considerations have been put forward concerning the mechanism of the stimulation of the biosynthesis of the gibberellins in media containing fats which are based on modern ideas concerning the metabolism of diterpenes in a culture ofF. moniliforme.Khimiya Prirodnykh Soedinenii, Vol. 5, No. 3, pp. 156–163, 1969     

Gibberellins and substances related to them

Summary 1. Column and thin-layer chromatography have been used to analyze the metabolite composition of the culture liquid ofFusarium moniliforme. 2. On fermentation in a medium containing sunflower oil and ammonium nitrate, the content of gibberellins of the A₃-A₁ group was 650–680 mg/l, of the gibberellins of the A₄-A₇ group 85–90 mg/l, and of gibberellin A₉ about 5 mg/l.Khimiya Prirodnykh Soedinenii, Vol. 2, No. 1, pp. 55–58, 1966     

Gibberellins and substances related to them

Summary 1. By means of preparative paper chromatography, an isomer of gibberelin A₃, the 1,3-lactone of 2, 3, 7-trihydroxy-1-methyl-8-methylene-⁴-gibbene-1, 10-dicarboxylic acid(II) has been isolated from the culture liquid ofFusarium moniliforme grown in a medium containing sunflower oil and ammonium nitrate.2. The formation of this product under fermentation conditions takes place hydrolytically by a nonenzymatic mechanism.3. A study of the physiological activity of the 1,3-lactone (II) has shown that the change in the position of the lactone cycle in ring A leads to a considerable decrease of the growth activity of this substance with respect to dwarf pea and lettuce, while it is retained with respect to cucumbers (as compared with the activity of gibberellin A₃).Khimiya Prirodnykh Soedinenii, Vol. 2, No. 2, pp. 114–120, 1966     

Benzoxazines and related compounds

The action of a nitrating mixture on 2-substituted 4,4-diethyl-4H-1,3-benzoxazines gives the corresponding 6-nitro derivatives, which can be isolated as such or as the hydrolysis products –N-acyl-,-diethyl-2-hydroxy-5-nitrobenzylamines. The latter cyclize to the corresponding 4H-1,3-benzoxazines under the influence of perchloric acid.See [1] for communication III.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 303–305, March, 1972.     

Benzoxazines and related compounds

A simple method has been elaborated for synthesizing 2-substituted 4,4-dialkyl-4H-1, 3-benzoxazines by the interaction between nitriles and o-oxyphenyldialkylcarbinols under the influence of acids.For part I, [1].     

Hydroacridines and related compounds

3,3-Dimethyl-2-oxa-1,2,3,4-tetrahydroacridine and its N-oxide and 3,3,6,6-tetramethyl-2,7-dioxa-sym-octahydroacridine N-oxide were synthesized. On heating with acetic anhydride, the N-oxides form, respectively, acetates of 3,3-dimethyl-2-oxa-1,2,3,4-tetrahydro-4-acridinol and 3,3,6,6-tetramethyl-2,7-dioxa-sym-octahydro-4-acridinol. Hydrolysis of the acetates gives the alcohols themselves. Oxidation of 3,3,6,6-tetramethyl-2,7-dioxa-sym-octahydro-4-acridinol acetate gives the corresponding N-oxide. Oxidation of 3,3,6,6-tetramethyl-2,7-dioxa-sym-octahydro-4-acridinol with manganese dioxide gives 3,3,6,6-tetramethyl-2,7-dioxa-sym-octahydro-4-acridinone.See [9] for communication VII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1218–1221, September, 1971.     

Hydroacridines and related compounds

The N-oxides of 2,4-diphenyl-5,6,7,8-tetrahydroquinoline, 2,4-diphenylpyrindane, and 7,7-dimethyl-2,4-diphenyl-6-oxa-5,6,7,8-tetrahydroquinoline were synthesized. On heating with acetic anhydride, the N-oxides form, respectively, acetates of 2,4-diphenyl-5,6,7,8-tetrahydro-8-quinolinol, 2,4-diphenyl-7-pyrindanol, and 7,7-dimethyl-2,4-diphenyl-6-oxa-5,6,7,8-tetrahydro-8-quinolinol; hydrolysis of the acetates gives the alcohols.See [10] for communication X.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1547–1551, November, 1972.     

Hydroacridines and related compounds

4-Benzoylhydroacridines were synthesized by the reaction of 4-lithiohydroacridines with benzonitrile or benzoyl chloride. Their capacity for keto-enol tautomerism was noted.See [1] for communication IX.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No, 7, pp. 984–986, July, 1972.     

Benzoxazines and related compounds

The reaction of 2-mercapto(and benzylthio)-α,α-dialkylbenzyl alcohols with nitriles under the influence of acids serves as a method for the synthesis of 2,4,4-trisubstituted 4H-1,3-benzothiazines.     

Hydroacridines and related compounds

2-Phenyl-7,7-dimethyl-5H-7,8-dihydropyrano[4,3-b]pyridine and its N-oxide were synthesized. Refluxing of the latter with acetic anhydride gives 2-phenyl-7,7-dimethyl-8-hydroxy-5H-7,8-dihydropyrano[4,3-b]pyridine acetate; hydrolysis of the acetate gives the alcohol.See [1] for communication XII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 824–825, June, 1973.     

Hydroacridines and related compounds

The effect of substituents in the 9 and 10 positions on the reductive capacities of 9,10-disubstituted decahydroacridines was established in the case of the reduction of organic dyes (Methylene Blue, Indigo Carmine, and Brilliant Green).See [1] for communication XV.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 969–972, July, 1977.