Regiospecific β-lactam ring-opening/recyclization reactions of N-aryl-3-spirocyclic-β-lactams catalyzed by a Lewis–Brønsted acids combined superacid catalyst system: a new entry to 3-spirocyclicquinolin-4(1H)-ones

Hu, Yinqiao; Fu, Xiaolan; Barry, Badru‐Deen; Bi, Xihe; Dong, Dewen

doi:10.1039/c1cc15881c

Cited by 21 publications

(10 citation statements)

References 20 publications

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“…15,18 Following the procedure described above for the synthesis of compound 1b , 2.14 g (20 mmol) of p -toluidine, 2.5 mL (24 mmol) of 3-bromopropanoyl chloride, and 1.57 g (16.5 mmol) of sodium tert -butoxide were employed to obtain 1.92 g of N -( p -tolyl)azetidin-2-one. To a solution of 1.61 g (10 mmol) of 1-( p -tolyl)azetidin-2-one in 20 mL of DCE at 0 °C was added 2 mL (22 mmol) of TfOH.…”

Section: Methodsmentioning

confidence: 99%

Formation of Acridones by Ethylene Extrusion in the Reaction of Arynes with β-Lactams and Dihydroquinolinones

et al. 2012

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N-Unsubstituted β-lactams react with a molecule of aryne by insertion into the amide bond to form a 2,3-dihydroquinolin-4-one, which subsequently reacts with another molecule of aryne to form an acridone by extrusion of a molecule of ethylene. 2,3-Dihydroquinolin-4-ones react under the same reaction conditions to afford identical results. This is the first example of ethylene extrusion in aryne chemistry.

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Section: Methodsmentioning

confidence: 99%

Formation of Acridones by Ethylene Extrusion in the Reaction of Arynes with β-Lactams and Dihydroquinolinones

et al. 2012

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“…The ring-opening/recyclization reaction of N-aryl-3-spirocyclic-β-lactams 109 has been described using the system FeCl 3 (30 mol%) and trifluoroacetic acid (TFA) (20 mol%), affording 3-spirocyclic quinolones 110 in excellent yields (Scheme 38) [41]. The reaction process is highly regioselective toward unsymmetrical substrates.…”

Section: Synthesis Of Six-membered Heterocyclesmentioning

confidence: 99%

Ring Expansions of β-Lactams and β-(thio)lactones

Alcaide

Almendros

Aragoncillo

2015

Topics in Heterocyclic Chemistry

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The skeleton of β-lactams and β-lactones is present in biologically active compounds. For example, the β-lactam ring is present in classical antibiotics such as penicillins and cephalosporins. On the other hand, there are several natural products containing a β-lactone moiety, with interesting inhibitory activity. In addition, both fragments are very useful synthetic intermediates for the preparation of cyclic and acyclic compounds. The ring strain present in both motifs is involved in this versatile reactivity. This chapter is devoted to the synthesis of five-to sevenmembered heterocycles by ring expansion of β-lactams and β-lactones. Different methodologies have been described, and the mechanism for the formation of the products has been discussed. In addition, the applicability of some of the processes has been demonstrated by the synthesis of fragments of natural or biologically relevant compounds. The contributions presented in this chapter have been selected mainly from the developments achieved in the last decade.

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“…The employment of a Lewis-Brønsted acid in combination with a superacid catalyst system promoted a regiospecific N1-C2 ring-opening reaction of N-aryl-3-spirocyclic-β-lactams 133 followed by a recyclization, providing an efficient entry to 3-spirocyclic quinolin-4(1H)-ones 134 in good to high yields (Scheme 40). 91…”

Section: Scheme 39mentioning

confidence: 99%

An update on the synthesis and reactivity of spiro-fused β-lactams

Thi¹,

D’hooghe²

2019

Arkivoc

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β-Lactam ring-containing compounds play a pivotal role in drug design and synthetic chemistry. Spirocyclic βlactams, representing an important β-lactam subclass, have recently attracted considerable interest with respect to new synthetic methodologies and pharmacological applications. The aim of this manuscript is to review the recent progress made in this field, covering publications disseminated between 2011 to 2018 concerning the synthesis and application of spirocyclic β-lactams. In the first part, new approaches to the synthesis of spirocyclic β-lactams, including Staudinger synthesis, cyclization and transformation reactions, will be presented. The reactivity and biological properties of spiro-β-lactams will be described in the second and third part, respectively.

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Regiospecific β-lactam ring-opening/recyclization reactions of N-aryl-3-spirocyclic-β-lactams catalyzed by a Lewis–Brønsted acids combined superacid catalyst system: a new entry to 3-spirocyclicquinolin-4(1H)-ones

Cited by 21 publications

References 20 publications

Formation of Acridones by Ethylene Extrusion in the Reaction of Arynes with β-Lactams and Dihydroquinolinones

Formation of Acridones by Ethylene Extrusion in the Reaction of Arynes with β-Lactams and Dihydroquinolinones

Ring Expansions of β-Lactams and β-(thio)lactones

An update on the synthesis and reactivity of spiro-fused β-lactams

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