Heterocycle-guided synthesis of m-hetarylanilines via three-component benzannulation

• Andrey R. Galeev,
• Maksim V. Dmitriev,
• Alexander S. Novikov and
• Andrey N. Maslivets

Beilstein J. Org. Chem. 2024, 20, 2208–2216, doi:10.3762/bjoc.20.188

• (Figure 1). On the other hand, 3,5-diarylanilines can be regarded as meta-terphenyls which are of great interest for material and coordination chemistry [5][6][7][8][9][10][11][12][13][14][15][16]. Moreover, compounds with diverse bioactivities and natural products contain the meta-terphenyl moiety as a

Isolation and biosynthesis of daturamycins from Streptomyces sp. KIB-H1544

• Yin Chen,
• Jinqiu Ren,
• Ruimin Yang,
• Jie Li,
• Sheng-Xiong Huang and
• Yijun Yan

Beilstein J. Org. Chem. 2022, 18, 1009–1016, doi:10.3762/bjoc.18.101

• skeleton exhibit a large number of structural diversity due to the differences of the center ring and the connection among rings. Structurally, most natural terphenyls are p-terphenyl derivatives consisting of a C-18 tricyclic or polycyclic C-18 aromatic skeleton. Diarylcyclopentenones, which possess a

• rare class of a tricyclic 6/5/6 system, could also belong to p-terphenyl derivatives from a biosynthetic perspective. To date, more than 230 natural products containing p-terphenyl have been unearthed in nature, among them many p-terphenyls were isolated from fungi, only a few were discovered from

• Streptomyces species [1][2][3][4]. Meanwhile, these types of compounds exhibit a broad spectrum of bioactivities, including antitumor [5][6], antibacterial [7][8], antioxidant [9][10][11][12], immunosuppressive [13], and antithrombotic activities [14]. The biosynthesis of the p-terphenyls has been studied

Recent advances in the syntheses of anthracene derivatives

• Giovanni S. Baviera and
• Paulo M. Donate

Beilstein J. Org. Chem. 2021, 17, 2028–2050, doi:10.3762/bjoc.17.131

• double cyclization and concluded that the reaction strongly depended on the position of the ethynyl groups in the terphenyl compounds. Terphenyls 125 were the most appropriate to prepare dibenzo[a,h]anthracenes in good yield (49–92%). AuCl was a notable catalyst because it maintained high cyclization

Acid-catalyzed rearrangements in arenes: interconversions in the quaterphenyl series

• Sarah L. Skraba-Joiner,
• Carter J. Holt and
• Richard P. Johnson

Beilstein J. Org. Chem. 2019, 15, 2655–2663, doi:10.3762/bjoc.15.258

• pirouette rearrangement of the reduced ring through a spirocyclic intermediate and then re-oxidation to phenanthrene. These reactions involve a complex series of proton and hydride transfers. Results and Discussion Beyond terphenyls, acid-catalyzed rearrangements pose limitations in the synthesis of

Substitution of fluorine in M[C₆F₅BF₃] with organolithium compounds: distinctions between O- and N-nucleophiles

• Anton Yu. Shabalin,
• Nicolay Yu. Adonin and
• Vadim V. Bardin

Beilstein J. Org. Chem. 2017, 13, 703–713, doi:10.3762/bjoc.13.69

• , the known 2,3,5,6-tetrafluorobiphenyl (14) [35][36] and 2,3,4,5-tetrafluorobiphenyl (15) [35][36] were obtained (Scheme 6). Then a mixture of borates 10-K, 11-K, 12-K, and 13-K was converted to biphenyls 14, 15, and terphenyls 20, 21, respectively, and characterized by 19F NMR spectroscopy, GC–MS and

Aspergiloid I, an unprecedented spirolactone norditerpenoid from the plant-derived endophytic fungus Aspergillus sp. YXf3

• Zhi Kai Guo,
• Rong Wang,
• Wei Huang,
• Xiao Nian Li,
• Rong Jiang,
• Ren Xiang Tan and
• Hui Ming Ge

Beilstein J. Org. Chem. 2014, 10, 2677–2682, doi:10.3762/bjoc.10.282

• previous chemical investigation of the bioactive secondary metabolites produced by the endophytic Aspergillus sp. YXf3 associated with Ginkgo biloba led to the isolation of new p-terphenyls and novel types of diterpenoids including pimarane-type diterpenoids (sphaeropsidins A and B, aspergiloids D and E

• investigation of Aspergillus sp. YXf3 revealed it is a pluripotent fungus which can produce different types of novel interesting metabolites, including p-terphenyls, pimarane, cleistanthane, norcleistanthane-type diterpenoids [7], and the “aspergilane”-type norditerpenoid 1. It is possible to propose that 1 is

Recent advances in the gold-catalyzed additions to C–C multiple bonds

• He Huang,
• Yu Zhou and
• Hong Liu

Beilstein J. Org. Chem. 2011, 7, 897–936, doi:10.3762/bjoc.7.103

• phenols (318–321) and unsymmetrical bi- and terphenyls (Scheme 54) [159]. The reaction is greatly affected by the electronic properties of dienyne acid. The regioselective 1,6-cyclization/decarboxylation sequence only takes place when a strong electron-donating group is not directly linked to the triple

Studies on Pd/NiFe₂O₄ catalyzed ligand-free Suzuki reaction in aqueous phase: synthesis of biaryls, terphenyls and polyaryls

• Sanjay R. Borhade and
• Suresh B. Waghmode

Beilstein J. Org. Chem. 2011, 7, 310–319, doi:10.3762/bjoc.7.41

• catalysis; nickel ferrite; polyaryls; Suzuki reaction; terphenyls; Introduction Recently, transition metal catalyzed cross-coupling protocols have generated immense interest owing to their versatile applications in organic synthesis [1][2][3][4]. The Pd catalyzed Suzuki reaction between aryl halides with

• (Table 4, entry 35). Whereas, activated aryl chlorides gave the coupling product in moderate yields after 24 h (Table 4, entries 33, 34). Recently, terphenyls have attracted attention due to their wide range of significant biological applications including potent immunosuppressant, neuroprotective

• , antithrombotic, anticoagulant and cytotoxic activities [44][45][46][47]. Polyphenyls are also an important structural element in liquid crystals and fluorescent compounds [48][49][50][51][52]. Terphenyls have been previously synthesized by the reaction of aryl- or benzylzinc reagents with functionalized biphenyl