+ Most Popular
Cunninghamia lanceolata plantations in China
Mammalian lairs in paleo ecological studies and palynology
Studies on technological possibilities in utilization of anhydrous milk fat for production of recombined butter-like products
Should right-sided fibroelastomas be operated upon?
Large esophageal lipoma
Apoptosis in the mammalian thymus during normal histogenesis and under various in vitro and in vivo experimental conditions
Poissons characoides nouveaux ou non signales de l'Ilha do Bananal, Bresil
Desensitizing efficacy of Colgate Sensitive Maximum Strength and Fresh Mint Sensodyne dentifrices
Administration of fluid by subcutaneous infusion: revival of a forgotten method
Tundra mosquito control - an impossible dream?
Schizophrenia for primary care providers: how to contribute to the care of a vulnerable patient population
Geochemical pattern analysis; method of describing the Southeastern limestone regional aquifer system
Incidence of low birth weights in a hospital of Mexico City
Graded management intensity of grassland systems for enhancing floristic diversity
Microbiology and biochemistry of cheese and fermented milk
The ember tetra: a new pygmy characid tetra from the Rio das Mortes, Brazil, Hyphessobrycon amandae sp. n. (Pisces, Characoidei)
Risk factors of contrast-induced nephropathy in patients after coronary artery intervention
Renovation of onsite domestic wastewater in a poorly drained soil
Observations of the propagation velocity and formation mechanism of burst fractures caused by gunshot
Systolic blood pressure in a population of infants in the first year of life: the Brompton study
Haematological studies in rats fed with metanil yellow
Studies on pasteurellosis. I. A new species of Pasteurella encountered in chronic fowl cholera
Dormancy breaking and germination of Acacia salicina Lindl. seeds
therapy of lupus nephritis. a two-year prospective study

The chemistry of coumarin derivatives synthesis of 3 alkyl 4 hydroxycoumarins by reductive fragmentation of 3 3' alkylidene 4 4' dihydroxybiscoumarins

The chemistry of coumarin derivatives synthesis of 3 alkyl 4 hydroxycoumarins by reductive fragmentation of 3 3' alkylidene 4 4' dihydroxybiscoumarins

Helvetica Chimica Acta 74(7): 1451-1458

ISSN/ISBN: 0018-019X

DOI: 10.1002/hlca.19910740708

Treatment of 3,3'-alkylidene-4,4'-dihydroxybis[coumarins] 1 with NaBH3CN in refluxing MeOH affords 3-alkyl-4-hydroxycoumarins 2 and 4-hydroxycoumarin (3; Scheme 1). The reaction might take place via hydride trapping of alkylidenechromandiones C formed from 1 in a retro-Michael reaction. Such a retro-Michael reaction of 1 might be biologically relevant. The presence of C during the reductive fragmentation 1 .fwdarw. 2 is suggested by Diels-Alder and nucleophilic trapping of the alkylidenechromandiones C as well as from cross-over experiments with coumarins other than 3 (see Scheme 2). The reductive fragmentation of 1 allows the chemo- and regioselective synthesis of a variety of 3-alkyl-4-hydroxycoumarins 2 (see Table).

Please choose payment method:

(PDF emailed within 0-6 h: $19.90)

Accession: 007877292

Download citation: RISBibTeXText

Related references

Synthesis, Bioassays and Field Evaluation of Hydroxycoumarins and their Alkyl Derivatives as Repellents or Kairomones for Aedes albopictus Skuse (Diptera: Culicidae). Journal of Chemical Ecology 44(3): 299-311, 2018

Studies on Synthesis of Coumarin Derivatives. Xxii. On the Preparation of N-Pyridyl-2-alkyl-8-oxo-8H-pyrano [3, 2-g] benzoxazole-7-carboxamide Derivatives. Chemical and Pharmaceutical Bulletin 17(9): 1955-1958, 1969

Studies on synthesis of coumarin derivatives part 22 on the preparation of n pyridyl 2 alkyl 8 oxo 8h pyrano 3 2 g benzoxazole 7 carboxamide derivatives. Chemical and Pharmaceutical Bulletin 17(9): 1955-1958, 1969

Cobalamin i as catalyst 6. formation and fragmentation of alkyl cobalamins the nucleophilic addition reductive fragmentation equilibrium. Helvetica Chimica Acta 63(2): 529-554, 1980

Synthesis of multiply substituted alkylidene silacyclohexadiene derivatives via palladium-catalyzed insertion of alkynes into alkylidene silacyclobutenes. Journal of Organic Chemistry 72(8): 3137-3140, 2007

Organic chemistry of dinuclear metal centres. XII: Synthesis, X-ray crystal structure, and reactivity of the Di-μ-alkylidene complex [Ru2(CO)2(μ-CHMe)(μ-CMe2)(η-C5H5)2]: alkylidene linking. Journal of the Chemical Society. Dalton Transactions (9): 1799-1805, 1989

Studies on synthesis of coumarin derivatives. 23. Synthesis and antibacterial activity of derivatives of 3-substituted-7-amino-4-hydroxy-coumarin. Chemical and Pharmaceutical Bulletin 17(11): 2384-2388, 1969

Coumarin to Isocoumarin: One-Pot Synthesis of 3-Substituted Isocoumarins from 4-Hydroxycoumarins and Benzyne Precursors. Organic Letters 19(3): 730-733, 2017

Natural product chemistry. CXXXXVII: Synthesis of some coumarin derivatives. Liebigs Annalen der Chemie (11): 1233-1235, 1991

Formation and ligand-based reductive chemistry of bridged bis-alkylidene scandium(iii) complexes. Chemical Science 8(10): 6852-6856, 2017

Studies on 4-hydroxycoumarins: I. The attempted resolution of warfarin. II. The chemistry of 3-acyl-4-hydroxycoumarins. Dissertation Abstracts 16(11): 2017-2018, 1956

Novel synthesis of 4 coumarin 3 yl 1 3 thiazole 2 coumarin 3 carbonylthieno 2 3 b pyridine and 2 coumarin 3 carbonylthiophene derivatives. Journal of Chemical Research (Synopses) (5): 154-155, 1992

Isohydroxylurea and its alkyl and alkylidene derivatives. Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft 292/64(1): 1-9, 1959

Studies on the synthesis of coumarin derivatives xxi on the preparation of 3 coumarin acetamide and 3 4 di hydro 2 oxo 2h benzopyran 3 carboxamide derivatives mouse. Yakugaku Zasshi: 755-760, 1968

GAP chemistry for pyrrolyl coumarin derivatives: a highly efficient one-pot synthesis under catalyst-free conditions. Green Chemistry 15(12): 3307-3311, 2013