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.

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.

Efficient synthesis of 1,2-benzisothiazoles from o-haloarylamidines and elemental sulfur via N–S/C–S bond formation under transition-metal-free conditions

2018 ◽  
Vol 20 (4) ◽  
pp. 827-831 ◽  
Author(s):  
Hao Xie ◽  
Guozheng Li ◽  
Feng Zhang ◽  
Fuhong Xiao ◽  
Guo-Jun Deng
Keyword(s):  
Transition Metal ◽  
Functional Groups ◽  
Elemental Sulfur ◽  
Bond Formation ◽  
Efficient Synthesis ◽  
Facile Synthesis ◽  
Good Tolerance ◽  
Metal Free

Facile synthesis of 1,2-benzisothiazoles from amidines and elemental sulfur via N–S/C–S bond formation under transition-metal-free conditions has been developed with good tolerance of a broad range of functional groups.

Facile synthesis of fused polycyclic compounds via intramolecular oxidative cyclization/aromatization of β-tetralone or β-tetralone oximes

2018 ◽  
Vol 16 (46) ◽  
pp. 9003-9010 ◽  
Author(s):  
Yan Jiang ◽  
Shuo-Wen Yu ◽  
Yi Yang ◽  
Ying-Le Liu ◽  
Xiao-Ying Xu ◽  
...  
Keyword(s):  
Oxidative Cyclization ◽  
Facile Synthesis ◽  
Polycyclic Compounds ◽  
Intramolecular Oxidative Cyclization

A mild and efficient NXS promoted intramolecular oxidative cyclization/aromatization of β-tetralone or β-tetralone oximes has been explored.

scholarly journals Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone

2021 ◽  
Vol 17 ◽  
pp. 2668-2679
Author(s):  
Ilya A P Jourjine ◽  
Lukas Zeisel ◽  
Jürgen Krauß ◽  
Franz Bracher
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Functional Groups ◽  
Oxidative Cyclization ◽  
Metal Free ◽  
Dehydrogenative Coupling ◽  
Protective Groups

Highly substituted fluorenones are readily prepared in mostly fair to good yields via metal- and additive-free TBHP-promoted cross-dehydrogenative coupling (CDC) of readily accessible N-methyl-2-(aminomethyl)biphenyls and 2-(aminomethyl)biphenyls. This methodology is compatible with numerous functional groups (methoxy, cyano, nitro, chloro, and SEM and TBS-protective groups for phenols) and was further utilized in the first total synthesis of the natural product nobilone.

Synthesis of Pyrrolo[1,2-a][1,6]- and [1,8]naphthyridines by Alkyne-Carbonyl Metathesis

Synthesis ◽  
2020 ◽  
Author(s):  
Peter Ehlers ◽  
Peter Langer ◽  
Marian Blanco Ponce ◽  
Silvio Parpart ◽  
Alexander Villinger ◽  
...  
Keyword(s):  
Heterocyclic Compounds ◽  
Metathesis Reaction ◽  
Synthetic Methodology ◽  
Facile Synthesis ◽  
Reaction Conditions ◽  
One Pot ◽  
Metal Free ◽  
Modular Synthesis

AbstractA concise and modular synthesis of pyrrolo[1,2-a][1,6]- and [1,8]naphthyridines by a one-pot two-step reaction consisting of electrophilic acylation followed by an alkyne-carbonyl-metathesis reaction as the final cyclization step is reported. This developed synthetic methodology allows the facile synthesis of these heterocyclic core structures in mainly high overall yields under metal-free conditions. Reaction conditions are carefully optimized and display a novel supplement to access these tricyclic heterocyclic compounds.

Metal-free oxidative cyclization of trifluoroacetimidohydrazides with methylhetarenes: a facile access to 3-hetaryl-5-trifluoromethyl-1,2,4-triazoles

2021 ◽  
Author(s):  
Xiao-Feng Wu ◽  
Zhengkai Chen ◽  
Jiajun Zhang ◽  
Tian-Hui Xu
Keyword(s):  
Oxidative Cyclization ◽  
Efficient Synthesis ◽  
Metal Free

A metal-free oxidative cyclization of trifluoroacetimidohydrazides with methylhetarenes for the efficient synthesis of 3-hetaryl-5-trifluoromethyl-1,2,4-triazoles has been developed. Notable features of this protocol include readily accessible starting materials, a broad substrate...

Transition-metal-free and facile synthesis of 3-alkynylpyrrole-2, 4-dicarboxylates from methylene isocyanides and propiolaldehyde

2021 ◽  
Author(s):  
Xiaoli Huo ◽  
Xiaojuan Chen ◽  
Liya Yu ◽  
Chong Zhang ◽  
Linghui Zeng ◽  
...  
Keyword(s):  
Transition Metal ◽  
Efficient Method ◽  
Transformation Process ◽  
Facile Synthesis ◽  
Direct Transformation ◽  
Metal Free

A transition-metal-free, facile and efficient method for the synthesis of 3-alkynylpyrrole-2, 4-dicarboxylates from methylene isocyanides and propiolaldehyde with moderate to good yields has been developed. The direct transformation process and...

An Efficient Substrate-Induced Method for the Synthesis of CF3-Substituted Cyclopropanes by Metal-Free Reaction of Trifluoromethyl Styrylisoxazoles with Nitromethane

Synthesis ◽  
2020 ◽  
Author(s):  
Feng Li ◽  
Hai Ma ◽  
Qing-he Zhao ◽  
Guang-hao Yu ◽  
Ye-chen Meng ◽  
...  
Keyword(s):  
Functional Groups ◽  
Phase Transfer ◽  
Cyclization Reaction ◽  
Metal Free ◽  
Tert Butyl ◽  
Pharmacological Interest ◽  
Substituted Cyclopropanes

AbstractA series of (trifluoromethyl)cyclopropanes (TFCPs) tolerating a broad range of functional groups, known as tert-butyl bioisosteres, have been obtained from the cyclization reaction between nitromethane­ and 5-[β-(trifluoromethyl)styryl]isoxazoles in 70–94% yields and 75:25 to 90:10 dr. This method offers practical access to this cyclopropyl moiety of pharmacological interest, employing an inorganic base under phase-transfer conditions.

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