Intramolecular Chalcogenylation of Isooxazolines Mediated by PhICl2 and Diorganyl Disulfides or Diselenides

Synthesis ◽  
2021 ◽  
Author(s):  
Fengxia Sun ◽  
Yunfei Du ◽  
Dongke Zhang ◽  
Jingran Zhang ◽  
Xiaoxian Li ◽  
...  
Keyword(s):  
Oxidative Cyclization ◽  
Excellent Yield ◽  
Intramolecular Oxidative Cyclization

AbstractReactive organosulfenyl chlorides (ArSCl) or selenenyl chlorides (ArSeCl), generated in situ from the reaction of PhICl2 with diorganyl disulfides or diselenides, enable the intramolecular oxidative cyclization/chalcogenylation of β,γ-unsaturated oximes, leading to the formation of a series of chalcogenylated isooxazolines in good to excellent yield.

Convenient Synthesis of Oxazolo[5,4-h]pyrrolo[4,3,2-de]quino­lones via Hypervalent Iodine Mediated Intramolecular Oxidative Cyclization

Synthesis ◽  
2017 ◽  
Vol 28 (19) ◽  
pp. 4517-4522
Author(s):  
Li-Ping Sun ◽  
Chun-Meng Wang ◽  
Sheng-Wei Yang ◽  
Kai-Xiang Tang ◽  
Tian-Hong Gao ◽  
...  
Keyword(s):  
Functional Groups ◽  
Practical Method ◽  
Oxidative Cyclization ◽  
Hypervalent Iodine ◽  
Air Atmosphere ◽  
Convenient Synthesis ◽  
Reaction Proceeds ◽  
Intramolecular Oxidative Cyclization

A convenient and practical method has been developed for the synthesis of substituted oxazolo[5,4-h]pyrrolo[4,3,2-de]quinolones via the intramolecular oxidative cyclization by using PIFA as oxidant and TMSOTf as additive in DCE under an air atmosphere. The reaction proceeds in good yields and has good functional groups tolerance.

Visible-light induced copper(i)-catalyzed oxidative cyclization of o-aminobenzamides with methanol and ethanol via HAT

2020 ◽  
Vol 18 (47) ◽  
pp. 9601-9605
Author(s):  
Mandapati Bhargava Reddy ◽  
Kesavan Prasanth ◽  
Ramasamy Anandhan
Keyword(s):  
Visible Light ◽  
Oxidative Cyclization

The activation of the C(sp3)–H of MeOH via HAT for the synthesis of quinazolinones has been achieved using an in situ generated ligand–copper-superoxo complex under visible light.

Metal-Free Oxidative C(sp3)–N Coupling by HBr and DMSO: A Novel Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones

Synlett ◽  
2018 ◽  
Vol 29 (07) ◽  
pp. 912-917 ◽  
Author(s):  
Parviz Ranjbar ◽  
Narjes Rezaei ◽  
Ehsan Sheikhi
Keyword(s):  
Oxidative Cyclization ◽  
Cyclization Reaction ◽  
Primary Amines ◽  
Isatoic Anhydride ◽  
Reaction Conditions ◽  
Coupling Process ◽  
Benzylic Alcohols ◽  
Metal Free ◽  
Novel Synthesis

A metal-free oxidative C(sp3)–N coupling process has been developed for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones. The reaction between primary amines, isatoic anhydride, and benzylic alcohols in the presence of HBr in DMSO at 80 °C affords 2,3-dihydroquinazolin-4(1H)-ones in excellent yields. Under these reaction conditions, benzylic alcohols react with in situ generated bromodimethylsulfonium bromide to form alkoxysulfonium intermediates. These intermediates undergo an oxidative cyclization reaction with primary amines and isatoic anhydride to produce the title products.

Facile synthesis of 3-amino-5-aryl-1,2,4-oxadiazoles via PIDA-mediated intramolecular oxidative cyclization

RSC Advances ◽  
2016 ◽  
Vol 6 (59) ◽  
pp. 54277-54280 ◽  
Author(s):  
Kuan Lu ◽  
Liancheng Duan ◽  
Boxuan Xu ◽  
Weile Yin ◽  
Di Wu ◽  
...  
Keyword(s):  
Functional Groups ◽  
Simple Procedure ◽  
Oxidative Cyclization ◽  
Ambient Condition ◽  
Facile Synthesis ◽  
Metal Free ◽  
Intramolecular Oxidative Cyclization

Advantages: ambient condition and simple procedure. Additive and metal free method. Up to 25 examples and 79% yield. Wide functional groups tolerance.

Oxidative Cyclization of β,γ-Unsaturated Carboxylic Acids Using Hypervalent Iodine Reagents: An Efficient Synthesis of 4-Substituted Furan-2-ones

Synthesis ◽  
2017 ◽  
Vol 49 (13) ◽  
pp. 2907-2912 ◽  
Author(s):  
Kensuke Kiyokawa ◽  
Satoshi Minakata ◽  
Kenta Takemoto ◽  
Shunsuke Yahata ◽  
Takumi Kojima
Keyword(s):  
Organic Chemistry ◽  
Carboxylic Acids ◽  
Present Method ◽  
Medicinal Chemistry ◽  
Oxidative Cyclization ◽  
Hypervalent Iodine ◽  
Efficient Synthesis ◽  
Substitution Pattern ◽  
Unsaturated Carboxylic Acids

The oxidative cyclization of β-substituted β,γ-unsaturated carboxylic acids using a hypervalent iodine reagent to provide 4-substituted furan-2-one products, is reported. In this cyclization, the use of a highly electrophilic PhI(OTf)2, which is in situ prepared from PhI(OAc)2 and Me3SiOTf, is crucial. Depending on the substitution pattern at the α-position of the substrates, furan-2(5H)-ones or furan-2(3H)-ones are produced. Thus, the present method offers a useful tool for accessing various types of 4-substituted furan-2-ones that are important structural motifs in the field of organic chemistry and medicinal chemistry.

Asymmetric epoxidation of alkenes catalyzed by novel chiral porphyrin metal complexes

2016 ◽  
Vol 20 (06) ◽  
pp. 730-737 ◽  
Author(s):  
Pachiannan Sakthipriya ◽  
Nallamuthu Ananthi
Keyword(s):  
Transition Metal ◽  
Metal Complexes ◽  
Transition Metal Complexes ◽  
Asymmetric Epoxidation ◽  
Excellent Yield ◽  
Chiral Epoxides ◽  
Epoxidation Reaction ◽  
Epoxidation Of Alkenes

Novel chiral porphyrin ligands were synthesized from four different chiral aldehydes. In situ transition metal complexes of these novel chiral porphyrin ligands were found to catalyze asymmetric epoxidation reaction of styrene possessing various substituents. The chiral epoxides were formed in excellent yield and ee.

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