205-82-3Relevant articles and documents
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Orchin,Reggel
, p. 505,507 (1947)
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Zinke,Pack
, p. 213,216 (1949)
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Regioselective Acid-Catalyzed Cyclodimerization of 1,2-Dihydronaphthalene. Mechanism of Formation and Single-Crystal X-ray Analysis of Two Octahydrobenzofluoranthenes
Dobbs, Thomas K.,Hertzler, Donald V.,Keen, Gary W.,Eisenbraun, Edmund J.
, p. 4769 - 4774 (1980)
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Three-Step Synthesis of Fluoranthenes through Pd-Catalyzed Inter- and Intramolecular C-H Arylation
Yamaguchi, Miyuki,Higuchi, Mayu,Tazawa, Kanae,Manabe, Kei
, p. 3967 - 3974 (2016/05/24)
A three-step synthetic method for the preparation of fluoranthenes, involving Miura's intermolecular C-H arylation, nonaflation, and intramolecular C-H arylation, has been developed. Various 1-naphthols and haloarenes were successfully used as substrates. Reaction conditions that afford high site selectivity have been developed for the intramolecular C-H arylation step.
Total synthesis of the natural product benzo[j]fluoranthene-4,9-diol: An approach to the synthesis of oxygenated benzo[j]fluoranthenes
Lahore, Santosh,Narkhede, Umesh,Merlini, Lucio,Dallavalle, Sabrina
, p. 10860 - 10866 (2013/11/19)
A synthetic sequence to the benzo[j]fluoranthene nucleus is described. Crucial steps of the procedure include a Suzuki coupling between appropriately substituted 2-bromo-acenaphthylene-1-carbaldehydes and 2-formylbenzeneboronates followed by McMurry ring closure. The synthesis represents a new approach to the benzo[j]fluoranthene ring system and specifically provides a method for the rapid preparation of differently substituted derivatives. Following this strategy, the first total synthesis of the recently isolated natural product benzo[j]fluoranthene-4,9-diol was carried out.
Efficient routes to acenaphthylene-fused polycyclic arenes/heteroarenes and heterocyclic fluoranthene analogues
Panda, Kausik,Venkatesh, Chelvam,Ila, Hiriyakkanavar,Junjappa, Hiriyakkanavar
, p. 2045 - 2055 (2007/10/03)
The acenaphthenone-derived a-oxoketene dithioacetal 2 has been subjected to various [3 + 3] aromatic and heteroaromatic annulation and other heterocyclization reactions previously developed in our laboratory, providing short and efficient routes to a diverse range of known and unknown acenaphtho-annulated linear and angular PAHs, heteroaromatics and five-membered heterocycles in good yields. Thus, benzo- and naphthoannulation of 2 with various allyl and benzyl Grignard reagents afforded substituted fluoranthenes 4a-c and benzo[k]fluoranthene 8, respectively, in good yields. Similarly, the parent benzo[j]fluoranthene 15a and its substituted derivative 16b have been synthesized by base-induced conjugate 1,4-addition of arylacetonitriles to 2, followed by acid-induced cyclization of the conjugate adducts 12a-b to give 13a-b and subsequent further transformations. The adducts obtained by 1,4-addition of anions derived from acetophenone and acenaphthenone were subjected to heterocyclization in the presence of ammonium acetate to give 8-arylacenaphtho[1,2-b]pyridines 18a-b and bis(acenaphtho)-annulated pyridine 20. Heterocyclization of 2 with bifunctional nucleophiles such as 2-picolyllithium and guanidinium nitrate afforded the corresponding acenaphtho[1,2-b]quinolizinium salt 23 and acenaphtho[1,2-d]pyrimidine 24, respectively, in high yields. Finally, acenaphtho[1,2-c]-fused five-membered heterocycles such as 7-(methylthio)acenaphtho[1,2-c]thiophene (25), 7-(methylthio)acenaphtho[1,2-c]furan (27) and 7-(methylthio)acenaphtho[1,2-c] pyrrole-2-carboxylic acid (30) were obtained in good yields by subjection of 2 to Simmons-Smith reaction conditions or by treatment with dimethylsulfonium methylide or glycinate dianion. Some of these newly synthesized PAHs or fused heterocycles were subjected to Raney Ni desulfurization to furnish sulfurfree compounds. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.