Synthesis of Azepine Derivatives by Rhodium‐Catalyzed Tandem 2,3‐Rearrangement/Heterocyclization

Nakamura, Itaru; Okamoto, Masashi; Sato, Yoshinori; Terada, Masahiro

doi:10.1002/ange.201205285

Cited by 28 publications

(4 citation statements)

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“…Accordingly, such monocyclic skeletons are generally constructed in good to moderate yields by olefin metathesis reactions, which inevitably require high‐dilution conditions (typically 0.002–0.005 M ) 9. 10 We have recently reported the use of Rh‐catalyzed cascade reactions for the efficient construction of seven‐membered nitrogen heterocyclic azepine oxides from O ‐propargylic cyclopropanecarboaldoximes (Scheme , n =0),11, 12 in which the starting oxime undergoes a 2,3‐rearrangement to form N ‐allenylnitrone intermediate A , then the formation of azarhodacycle B occurs, followed by ring expansion of the strained cyclopropyl group. Accordingly, we envisioned that our methods could be extended to the efficient construction of the elusive monocyclic azocine skeletons, without the use of high‐dilution conditions, starting with a readily accessible cyclobutyl moiety as the ring‐expanding functional group (Scheme , n =1) 13.…”

Section: Methodsmentioning

confidence: 99%

“…Notably, product 2 a was readily separated from triarylphosphine oxides by using silica gel chromatography. In contrast, the previous azepine oxide synthesis11 required the use of water‐soluble phosphine TPPMS (TPPMS=sodium diphenylphosphinobenzene‐3‐sulfonate) because of difficulties in the purification steps 16…”

Section: Methodsmentioning

confidence: 99%

“…Cbz = carbobenzyloxy. azepine oxide synthesis [11] required the use of water-soluble phosphine TPPMS (TPPMS = sodium diphenylphosphinobenzene-3-sulfonate) because of difficulties in the purification steps. [16] Next, the reactions of various E oximes (E)-1 were carried out, as summarized in Table 2, using the optimized reaction conditions (Table 1, entry 9).…”

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confidence: 99%

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Efficient Synthesis of Eight‐Membered Nitrogen Heterocycles from O‐Propargylic Oximes by Rhodium‐Catalyzed Cascade Reactions

Nakamura

Sato

Takeda

et al. 2014

Chemistry A European J

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Efficient Synthesis of Eight‐Membered Nitrogen Heterocycles from O‐Propargylic Oximes by Rhodium‐Catalyzed Cascade Reactions

Nakamura

Sato

Takeda

et al. 2014

Chemistry A European J

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“…The goal of the pharmacological assay was to find the first instance of a novel PDE4B inhibitor based on 1H-benzo[d]azepin-2(3H)-one. Similarly, the 7-membered heterocyclic compounds can be synthesized to act like as antioxidant, anticonvulsant, antiallergic, herbicidal and Antibacterial etc (40).…”

Section: Potential Agents Against Inflammationmentioning

confidence: 99%

Synthesis of 7-Membered Heterocyclic Compounds and Their Biological Activity

Rana,

Ansari

2023

J. Phys.: Conf. Ser.

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Heterocyclic compounds are an important class of organic compound. Owing to their usefulness in synthetic processes, numerous heterocyclic compounds are currently known, and this number is growing quickly. The uses of heterocyclic compounds are numerous. They are mostly used as veterinary goods, agricultural chemicals, and medications. Additionally, they are used as sanitizers, cleansers, antioxidants, corrosion inhibitors, co-polymers, and dye ingredients. The ring of a heterocyclic compound contains at least two unique components as members. On such a cyclic ring, the frequent heteroatoms are oxygen, nitrogen as well as sulphur. The most stable heterocyclic compound is a 7-membered ring over other heterocyclic compounds. Hence this article specifically reviews the synthesization of 7-membered heterocyclic compounds and their biological activity. The set of reviewed articles chosen in the current attempt is selected after the rigorous process of evaluating each aspect related to the 7-membered heterocyclic compound. This review paper will be of great interest to scientific groups working in the field of organic molecule synthesis and development.

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Recent Advances in Gold‐Catalyzed N‐ and O‐Functionalizations of Alkynes with Nitrones, Nitroso, Nitro and Nitroxy Species

2016

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Nitrone and nitroso species are versatile compounds to react with alkenes or butadienes to access five-ands ix-membered nitroxy (N À O) containing heterocycles,t oo ffer further access to acyclic 1,3-and 1,4-aminoa lcohols after facile cleavage of the N À Ob onds.T he N-andO -functionalizationso f alkynes with nitroneso rn itroso species have been explored less wellt han the corresponding alkene reactions.I nr ecent decades,g old catalysts have enabled the electrophilic activation of alkynes with weak nucleophiles.T hisr eview summarizes recent progress to implement N-and O-functionalizations of alkynes with common N À Oc ontainings pecies including nitrone,n itroso,n itro and other nitroxy derivatives.R eportedr eactions include the following three topics:( i) 1,2-difunctionalizations,( ii)c yclizations and (iii)c ycloaddition or annulation reactions. Ther eview is organized according to the typeso fn ucleophiles,f ollowed by reactions of the mentioned types.E nantioselective functionalizations of alkynes with these nitroxy nucleophiles are also included.

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Synthesis of Azepine Derivatives by Rhodium‐Catalyzed Tandem 2,3‐Rearrangement/Heterocyclization

Cited by 28 publications

References 50 publications

Efficient Synthesis of Eight‐Membered Nitrogen Heterocycles from O‐Propargylic Oximes by Rhodium‐Catalyzed Cascade Reactions

Efficient Synthesis of Eight‐Membered Nitrogen Heterocycles from O‐Propargylic Oximes by Rhodium‐Catalyzed Cascade Reactions

Synthesis of 7-Membered Heterocyclic Compounds and Their Biological Activity

Recent Advances in Gold‐Catalyzed N‐ and O‐Functionalizations of Alkynes with Nitrones, Nitroso, Nitro and Nitroxy Species

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