Notes - Synthetic Experiments in the Furocoumarin Series

Naik, Radhey Mohan; Thakor, V. M.

doi:10.1021/jo01363a606

Cited by 14 publications

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“…Of the many approaches to the construction of furocoumarins [12][13][14][15], we selected the MacLeod method for forming the psoralen system that is based on cyclization in alkaline medium of 7-(2-oxoethyl)coumarins. In most instances this leads exclusively to linear furocoumarins (psoralen-type furocoumarins) because the 6-position of the coumarin ring is more highly activated than the 8-position [16,17].…”

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“…The alkylating agents in this synthesis were chloroacetone (3,4), 1-chloropinacolone (5, 6), 3-chloro-2-butanone (7,8), 2-bromopropiophenone (9, 10), phenacylbromide (11,12), 4-fluorophenacylchloride (13,14), 4-chlorophenacylbromide (15,16), 4-bromophenacylbromide (17,18), 4-methoxyphenacylbromide (19, 20), 3-methoxyphenacylbromide (21, 22), and 2-chlorocyclohexanone (23, 24). PMR spectra of 3-24 typically had signals characteristic of the corresponding alkyl substituents and coumarin system.…”

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Modified coumarins. 24. Synthesis of cycloheptane-annellated tetracyclic furocoumarins

Garazd

Ogorodniichuk

et al. 2006

Chem Nat Compd

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Furocoumarins comprise natural compounds with a variety of structures that in most instances are derivatives of the linear furocoumarin psoralen [1]. Natural furocoumarins and their synthetic analogs have various physiological activities that depend on the chemical structure. Thus, furocoumrains with carbocycles annellated at the 5,6-positions exhibit photoantiproliferative [2-5] and cardiotropic [6] activities and act as CNS stimulants [6].In continuation of research on the synthesis and properties of furocoumarins [6-9], herein we report the preparation of tetracyclic psoralen-type furocoumarins containing a cycloheptane ring annellated to the 5,6-positions of a furo[3,2-g]chromen-7-one.3-Hydroxy-8,9,10,11-tetrahydrocyclohepta[c]chromen-6-one (1) and its 4-methyl analog (2) that were necessary for further transformations were prepared by Pechmann condensation of resorcinol and 2-methylresorcinol, respectively, with methyl-2-oxo-1-cycloheptanecarboxylate in the presence of conc. H 2 SO 4 at 0°C [10, 11]. 1, 23, 45: R = H; 2, 24, 46: R = Me; 3, 25: R = H, R 1 = Me; 4, 26: R = R 1 = Me, 5, 27: R = H, R 1 = t-Bu; 6, 28: R = Me, R = t-Bu; 7, 29: R = H, R 1 = R 2 = Me; 8, 30: R = R 1 = R 2 = Me, 9, 31: R = H, R 1 = Me, R 2 = Ph; 10, 32: R = R 1 = Me, R 2 = Ph; 11, 33: R = H, R 1 = Ph; 12, 34: R = Me, R 1 = Ph, 13, 35: R = H, R 1 = 4-FPh; 14, 36: R = H, R 1 = 4-FPh; 15, 37: R = H, R 1 = 4-ClPh; 16, 38: R = Me, R 1 = 4-ClPh 17, 39: R = H, R 1 = 4-BrPh; 18, 40: R = Me, R 1 = 4-BrPh; 19, 41: R = H, R 1 = 4-MeOPh; 20, 42: R = Me, R 1 = 4-MeOPh 21, 43: R = H, R 1 = 3-MeOPh; 22, 44: R = Me, R 1 = 3-MeOPh

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Modified coumarins. 24. Synthesis of cycloheptane-annellated tetracyclic furocoumarins

Garazd

Ogorodniichuk

et al. 2006

Chem Nat Compd

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“…Modification of the dibenzo[b,d]pyran-6-one system by adding a furan ring was expected to produce new biologically active compounds based on natural bioregulators.Of the numerous possibilities for constructing the furocoumarins [11][12][13][14], we selected the MacLeod method for forming the psoralen system that is based on cyclization in alkaline medium of 7-(2-oxoethyl)coumarin derivatives. In most instances this led exclusively to linear furocoumarins (psoralen-type furocoumarins) since the 6-position of the coumarin ring is more strongly activated than the 8-position [15,16].…”

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confidence: 99%

“…The alkalyating agents in this synthesis were chloroacetone (3,4), 1-chloropinacolone (5, 6), 3-chlorobutan-2-one (7, 8), 2-bromopropiophenone (9, 10), phenacylbromide (11,12), and 2-chlorocyclohexanone (13,14).…”

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Modified coumarins. 15. Condensed psoralen derivatives based on substituted dibenzo[b,d]pyran-6-ones

Garazd

Khilya

2004

Chem Nat Compd

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Natural and synthetic dibenzo [b,d]pyran-6-ones are known to possess a wide spectrum of biological activity, in particular, insecticidal [1], antimicrobial [2], antiviral [3], and anti-hepatitic [4], and to act as inhibitors of aldosereductase [5], tyrosinekinase [6], and 3-phosphoglyceratekinase [7].In continuation of the synthesis and investigation of the properties of condensed furocoumarins [8-10], we prepared new tetracyclic psoralen analogs based on 3-methoxybenzo[c]furo[3,2-g]chromen-5-one. Modification of the dibenzo[b,d]pyran-6-one system by adding a furan ring was expected to produce new biologically active compounds based on natural bioregulators.Of the numerous possibilities for constructing the furocoumarins [11][12][13][14], we selected the MacLeod method for forming the psoralen system that is based on cyclization in alkaline medium of 7-(2-oxoethyl)coumarin derivatives. In most instances this led exclusively to linear furocoumarins (psoralen-type furocoumarins) since the 6-position of the coumarin ring is more strongly activated than the 8-position [15,16].

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Furocoumarins

1967

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Notes - Synthetic Experiments in the Furocoumarin Series

Cited by 14 publications

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Modified coumarins. 24. Synthesis of cycloheptane-annellated tetracyclic furocoumarins

Modified coumarins. 24. Synthesis of cycloheptane-annellated tetracyclic furocoumarins

Modified coumarins. 15. Condensed psoralen derivatives based on substituted dibenzo[b,d]pyran-6-ones

Furocoumarins

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