Modified Coumarins. 7. Synthesis and Biological Activity of Mannich Bases of Substituted 7,8,9,10-Tetrahydrobenzo[c]chromen-6-ones

Condensation of 1- and 3-hydroxy-7,8,9,10-tetrahydrobenzo[c]chromen-6-ones with substituted 1,1- diaminomethanes produced Mannich bases containing a dialkylaminomethyl group in the 2- and 4-positions of 7,8,9,10-tetrahydrobenzo[c]chromen-6-one. Pharmacological screening of 2-chloro-3-hydroxy-4-(1- pyrrolidinylmethyl)-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one in Wistar rats showed that it possesses low toxicity and acts as a stimulant of the central and peripheral nervous systems with indications of neuroleptic and tranquilizing activities.     

Modified Coumarins. 11. Synthesis and Biological Activity of Mannich Bases of Substituted 1,3-Dihydrocyclopenta[c]chromen-4-ones

Mannich bases containing the dialkylaminomethyl group in the 6- and 8-positions of 2,3-di-hydrocyclopenta[c]chromen-4-ones were prepared by condensation of 7- and 9-hydroxy-2,3-dihydrocyclopenta[c]chromen-4-ones with substituted 1,1-diaminomethanes. The effects of 8-chloro-7-hydroxy-6-(1-pyrrolidinylmethyl)-2,3-dihydrocyclopenta[c]chromen-4-one and 8-chloro-7-hydroxy-6-(morpholinomethyl)-2,3-dihydrocyclopenta[c]chromen-4-one on the central and peripheral nervous systemwere defined and enable the presence of tranquilizing and neuroleptic properties to be predicted.     

Modified Coumarins. 16. Cyclohexane-Annelated Analogs of Pyranocoumarins

Modified derivatives of angular and linear pyranocoumarins containing a condensed cyclohexane moiety were prepared by fusing a 2,2-dimethyltetrahydropyran ring to the coumarin system and annelating a pyrone ring to derivatives of 2,2-dimethylchromane. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 313–318, July–August, 2005.     

Modified Coumarins. 9. Synthesis of Amino-Acid Derivatives of 3-(2,3,5-Trimethyl-7-oxofuro[3,2-g]chromen-6-yl)propanoic Acid

Furocoumarins modified by amino acids were prepared by condensation of the N-hydroxysuccinimide ester of 3-(2,3,5-trimethyl-7-oxofuro[3,2-g]chromen-6-yl)propanoic acid with amino acids.     

Modified Coumarins. I. Synthesis of 5-Phenyl-7H-furo[2, 3-g]chromen-7-ones and 9-Phenyl-7H-furo-[2, 3-f]chromen-7-ones

5-Phenyl-7H-furo[2,3-g]chromen-7-ones and 9-phenyl-7H-furo-[2,3-f]chromen-7-ones, new analogs of psoralen and allopsoralen, are synthesized from 7-hydroxy- and 5-hydroxy-4-phenylcoumarins     

MODIFIED COUMARINS. 3. PSORALEN AND ALLOPSORALEN ANALOGS

1,2,3,4-Tetrahydro-5H-benzo[c]furo[3,2-g]chromen-5-ones and 8,9,10,11-tetrahydro-7H-benzo[c]furo[2,3-f]chromen-7-ones, analogs of psoralen and allopsoralen, were synthesized from 1-hydroxy- and 3-hydroxy-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-ones.     

Modified Coumarins. 4. Synthesis and Biological Properties of Cyclopentaneannelated Furocoumarins

Psoralen and allopsoralen analogs that contain an annelated cyclopentane were synthesized from 7-hydroxyand 9-hydroxy-1,2,3,4-tetrahydrocyclopenta[c]chromen-4-ones. 9-Phenyl-1,2,3,4-tetrahydrocyclopenta[c]furo[3,2-g]chromen-4-one exhibited low toxicity, acted as a CNS stimulant, and exhibited cardiotropic activity.     

Microwave-Assisted Synthesis and Antifungal Activities of Polysubstituted Furo[3,2-c]chromen-4-ones and 7,8,9,10-Tetrahydro-6H-benzofuro[3,2-c]chromen-6-ones

An efficient and novel microwave-assisted synthesis of furo[3,2-c]chromen-4-ones and 7,8,9,10-tetrahydro-6H-benzofuro[3,2-c]chromen-6-ones via 4-hydroxycoumarins with α-chloroketones or α-bromocyclohexanone in the presence of acetic acid (AcOH)/ammonium acetate (NH₄OAc) using DMF as solvent under microwave irradiation is described. Systematically, antifungal biological tests showed that most of the compounds exhibited potent antifungal activity against Botrytis cinerea, Collecterichum capsica, Alternaria solani, Gibberella zeae, and Rhizoctorzia solani at the concentration of 50 µg/mL. The corresponding EC50 values of these analogues have been detected, and compound 4i showed better antifungal activity against tested fungi Botrytis cinerea and Collecterichum capsica than the reference Osthol.     

Modified Coumarins. 6. Synthesis of Substituted 5,6-Benzopsoralens

Substituted 5H-benzo[c]furo[3,2-g]chromen-5-ones, modified analogs of psoralen that contain a benzene ring annelated at the 5,6-position of a furo[3,2-g]chromen-7-one system, were synthesized from 3-hydroxy- 6H-benzo[c]chromen-6-ones.     

Facile synthetic route to benzo[c]chromenones and thieno[2,3-c]chromenones

Convenient two-step procedure for the synthesis of fused chromenone derivatives was developed. Reduction of the obtained in the Meerwein arylation reaction aryl- and thienylquinones allowed to construct 6H-benzo[c]chromene-6-ones and 4H-thieno[2,3-c]chromen-4-one in a more cost- and time-effective manner in comparison with already known methods. The obtained products have provided a new entry to chromenone derivatives.     

Modified coumarins. 13. Synthesis of cyclopentane-annelated pyranocoumarins

Modified pyranocoumarins containing a condensed cyclopentane fragment were synthesized by adjoining a 2,2-dimethyltetrahydropyran ring to a 2,3-dihydrocyclopenta[c]chromen-4-one system and annelation of a pyrone ring to a 2,2-dimethylchromane.Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 352–357, September–October, 2004.     

One-Pot Synthesis and Fungicidal Activities of Derivatives of Imidazo [2,1-b]-1,3,4-thiadiazol-5(6H)-one

The isothiocyanates 2, obtained from aza-Wittig reactions of vinyliminophosphoranes 1 with CS ₂ , reacted with hydrazine to give 3-amino-2-thioxo-4-imidazolidinones 4. One-pot reactions of 4, aromatic isocyanates, Ph ₃ P, C ₂ Cl ₆ , and Et ₃ N generated imidazo[2,1-b]-1,3,4-thiadiazol-5(6H)-ones 7. Compound 7 exhibited good fungicidal activities, especially against Sclerotinia sclerotiorum de Bary and Botrytis Cinerea Pers.     

Synthesis of some 5H-benzo[a]phenothiazin-5-one derivatives

Several substituted 6-anilino-5H-benzo[a]phenothiazin-5-one derivatives were prepared by condensation of substituted 1,4-naphthoquinones with 2-aminobenzenethiol in pyridine. The reduction and acetylation of the resulting compounds were also investigated.

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Synthese einiger 5H-Benzo[a]phenothiazin-5-on-Derivate

Zusammenfassung Es wurden mittels Kondensation substituierter 1,4-Naphthochinone mit 2-Aminothiophenol in Pyridin einige substituierte 6-Anilino-5H-benzo[a]phenothiazin-5-one dargestellt. Die Reduktion und Acetylierung der resultierenden Verbindungen wurde ebenfalls untersucht.

     

Modified Coumarins. 18. Synthesis of Angular Dihydropyranocoumarins Containing Amino Acids and Peptides

Angular dihydropyranocoumarins containing natural and synthetic amino acids and dipeptides were synthesized using activated esters. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 422–427, September–October, 2005.     

Reaction of 3-Cyano-2-diazo-4,5,6,7-tetrahydrobenzo[ b ]thiophene with 3-Imino-butyronitrile: Synthesis of Pyridazines,Thiophenes and Their Fused Derivatives

The reaction of the 3-cyano-2-diazo-4,5,6,7-tetrahydrobenzo[ b ]thiophene 1 with 3-imino-butyronitrile 2 gave the azo derivative ( 3 ). The reactivity of the latter product toward different reagents was studied to give fused derivatives with potential biological activities.     

The photochemical synthesis of 6-acyl-5H-benzo[a]phenoxazin-5-ones

6-Acyl-5H-benzo[a]phenoxazin-5-ones were prepared by the photochemical reaction of 5H-benzo[a]phenoxazin-5-one with aldehydes.

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Die photochemische Synthese von 6-Acyl-5H-benzo[a]phenoxazin-5-one (Kurze Mitteilung)

Zusammenfassung Die Titelverbindungen wurden mittels photochemischer Reaktion von 5H-Benzo[a]phenoxazin-5-onen mit Aldehyden hergestellt.

     

Ion Complexation Properties of Calix[6]Arene Derivatives: I. 1,4-Calix[6]Crown-4 Derivatives

Abstract

A series of 1,4-p-tert-butyl-calix[6]crown-4 tetraesters, tetraamides, tetraacids with defined conformation have been synthesized, and their complexation properties towards metal ions and alkyl ammonium ions were investigated systematically. It was found that 1,4-p-tert-butyl-calix[6]crown-4 tetraethylester (3a) and 1,4-p-tert-butyl-calix[6]benzocrown-4 tetramethyl-ester (4b) show high selectivity towards Na⁺, Li⁺, respectively and all of them exhibit high complexation abilities towards Et₂NH₂ ⁺ cation.     

Synthesis and Characterization of New Chalcone Derivatives from cis-Bicyclo[3.2.0]hept-2-en-6-one

A series of chalcone derivatives (3a–k) were prepared via the reaction of cis-bicyclo[3.2.0]hept-2-en-6-one (1) with the respective arylaldehydes (2a–k) and were then characterized by Fourier transform infrared (FT-IR), ¹H NMR, ¹³C NMR, and elemental analyses.     

Modified Coumarins. 8. Synthesis of Substituted 5-(4-Methoxyphenyl)-7H-furo[3,2-g]chromen-7-ones

The MacLeod method was used to synthesize a series of substituted 5-(4-methoxyphenyl)-7H-furo[3,2- g]chromen-7-ones, modified analogs of psoralen, from 7-hydroxy-4-(4-methoxyphenyl)coumarins.     

Modified coumarins. 26. Synthesis of angular dihydrooxazinocoumarins from 3-hydroxy[<Emphasis Type="Italic">b,d</Emphasis>]pyran-6-one

N-Substituted angular pyranodihydrobenzoxazines were prepared by condensation of 3-hydroxy-dibenzo[b,d]pyran-6-one with various primary amines and two equivalents of formaldehyde in the presence of 4-N,N-dimethylaminopyridine as base. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 14–17, January–February, 2007.