Metal-Free Cascade Methylation/Cyclization of N-Alkyl-N-methacryloylbenzamides with Dicumyl Peroxide

Synlett ◽  
2017 ◽  
Vol 29 (05) ◽  
pp. 617-620 ◽  
Author(s):  
Yan-Ning Niu ◽  
Xiao-Feng Xia ◽  
Yuan Yuan
Keyword(s):  
Free Radical ◽  
Dicumyl Peroxide ◽  
Metal Free ◽  
Wide Range ◽  
Radical Cascade ◽  
Convenient Access

A metal-free radical cascade methylation/cyclization of a wide range of N-alkyl-N-methacryloylbenzamides by using dicumyl peroxide as the methylating reagent provides a convenient access to a series of methylated isoquinoline-1,3-diones in moderate yields.

Metal-free radical cascade dichloromethylation of activated alkenes using CH2Cl2: highly selective activation of the C–H bond

RSC Advances ◽  
2014 ◽  
Vol 4 (110) ◽  
pp. 64855-64859 ◽  
Author(s):  
Yunfei Tian ◽  
Zhong-Quan Liu
Keyword(s):  
Free Radical ◽  
Dicumyl Peroxide ◽  
Cascade Process ◽  
Selective Activation ◽  
Metal Free ◽  
Efficient Access ◽  
Radical Cascade

A dicumyl peroxide-initiated highly selective activation of the (sp3)C–H bond in dichloromethane (DCM, CH2Cl2) has been achieved, which allows efficient access to dichloronated oxindoles via a free-radical cascade process.

A metal-free radical cascade reaction of phosphine oxides with 2-aryloxy phenylacetylenes to assemble diphosphonyl xanthene derivatives

2021 ◽  
Author(s):  
Tao Fan ◽  
Yan Liu ◽  
Caina Jiang ◽  
Yanli Xu ◽  
Yan-Yan Chen
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Cascade Reaction ◽  
Phosphine Oxides ◽  
Metal Free ◽  
Mild Conditions ◽  
Xanthene Derivatives ◽  
Reaction Proceeds ◽  
Radical Cascade

A radical cascade reaction of 2-aryloxy phenylacetylene with phosphine oxides promoted by K2S2O8 was developed, provided diphosphonyl xanthenes as products. This reaction proceeds under transition metal-free and mild conditions with...

(Diacetoxyiodo)benzene-Mediated Transition-Metal-Free Amination of C(sp3)–H Bonds Adjacent to Heteroatoms with Azoles: Synthesis of N-Alkylated Azoles

Synlett ◽  
2018 ◽  
Vol 29 (18) ◽  
pp. 2432-2436 ◽  
Author(s):  
Can Jin ◽  
Weike Su ◽  
Bin Sun ◽  
Zhiyang Yan
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Coupling Reaction ◽  
Metal Catalyst ◽  
Metal Free ◽  
Alternative Method ◽  
Dehydrogenative Coupling ◽  
Wide Range ◽  
Ready Access

A novel PhI(OAc)2-mediated cross-dehydrogenative coupling reaction of α-C(sp3)–H bonds adjacent to a hetero atom with various azoles has been developed, which provides an alternative method for constructing C–N bonds with high atom efficiency. This new protocol requires no metal catalyst and it provides ready access to a wide range of N-alkylated azole derivatives in moderate to excellent yields by using commercially available PhI(OAc)2 as the sole oxidant. Furthermore, the method is effective on a gram scale, which highlights the practicality of this transformation. The result of radical-captured experiments indicated that the transformation might involve a free-radical pathway.

Peroxide-Mediated Oxidative Radical Cyclization to the Quinazolinone System: Efficient Syntheses of Deoxyvasicinone, Mackinazolinone and (±)-Leucomidine C

Synthesis ◽  
2020 ◽  
Author(s):  
Luis D. Miranda ◽  
Jazmín García-Ramírez
Keyword(s):  
Natural Products ◽  
Free Radical ◽  
Total Synthesis ◽  
Radical Cyclization ◽  
Oxidative Cyclization ◽  
Dicumyl Peroxide ◽  
Cyclization Process ◽  
Radical Cascade ◽  
Oxidative Radical Cyclization

AbstractAn efficient protocol for obtaining fused quinazolinones through an oxidative free-radical cyclization under metal- and tin-free conditions is described. The oxidative cyclization of various N-3-ω-iodoalkyl derivatives to provide tricyclic systems using dicumyl peroxide as the sole reagent is studied. The method then is employed for the syntheses of 5-, 6-, and 7-membered fused quinazolinone analogues, including the natural products deoxyvasicinone and mackinazolinone. A xanthate-based oxidative radical cascade addition/cyclization process that allows the production of new menthol- and testosterone-quinazolinone conjugates, as well as the first total synthesis of leucomidine C, are also reported.

Metal-free radical cascade chloromethylation of unactivated alkenes: synthesis of polychloro-substituted indolines

2018 ◽  
Vol 16 (32) ◽  
pp. 5752-5755 ◽  
Author(s):  
Changduo Pan ◽  
Du Gao ◽  
Zhenkun Yang ◽  
Chao Wu ◽  
Jin-Tao Yu
Keyword(s):  
Free Radical ◽  
Metal Free ◽  
Radical Cascade

The di- and trichloromethylation of N-allyl anilines with CH2Cl2, CHCl3 and CCl4 was developed, leading to di- and trichloromethylated indolines.

Metal-free radical C–H methylation of pyrimidinones and pyridinones with dicumyl peroxide

2017 ◽  
Vol 19 (4) ◽  
pp. 919-923 ◽  
Author(s):  
Pei-Zhi Zhang ◽  
Jian-An Li ◽  
Ling Zhang ◽  
Adedamola Shoberu ◽  
Jian-Ping Zou ◽  
...  
Keyword(s):  
Free Radical ◽  
Dicumyl Peroxide ◽  
Metal Free

A method for free radical methylation of pyrimidinones and pyridinones with dicumyl peroxide under metal-free conditions is introduced. A 50 g-scale reaction could be performed safely. The product was separated by crystallization and the byproducts were recovery by distillation.

Transition-metal-free oxidative carboazidation of acrylamides via cascade C–N and C–C bond-forming reactions

2014 ◽  
Vol 12 (25) ◽  
pp. 4329-4334 ◽  
Author(s):  
Jun Qiu ◽  
Ronghua Zhang
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Efficient Method ◽  
Bond Formation ◽  
Cascade Process ◽  
Metal Free ◽  
Bond Forming ◽  
Bond Forming Reactions ◽  
Radical Cascade ◽  
Novel Strategy

A novel transition-metal-free oxidative carboazidation of acrylamides using inexpensive NaN3 and K2S2O8 was achieved, which not only provided an efficient method to prepare various N3-substituted oxindoles, but also represented a novel strategy for C–N and C–C bond formation via a free-radical cascade process.

Synthesis of Indolo[2,1-α]isoquinoline Derivatives via Metal-free Radical Cascade Cyclization

2021 ◽  
Author(s):  
Jianzhong Chen ◽  
Hu Xu-yang ◽  
Haifeng Xu ◽  
Qiang Chen ◽  
You-lu Pan
Keyword(s):  
Free Radical ◽  
Core Structure ◽  
Metal Free ◽  
Cascade Cyclization ◽  
Radical Cascade ◽  
Isoquinoline Derivatives

In the present studies, we described a convenient and efficient protocol for the synthesis of the indolo[2,1-]isoquinoline core structure through the reaction of 2-aryl-N-acryloyl indoles and aryl or alkyl -keto...

A Free-Radical Cascade Methylation/Cyclization of N-Arylacrylamides and Isocyanides with Dicumyl Peroxide

2014 ◽  
Vol 16 (21) ◽  
pp. 5670-5673 ◽  
Author(s):  
Zhengbao Xu ◽  
Chaoxian Yan ◽  
Zhong-Quan Liu
Keyword(s):  
Free Radical ◽  
Dicumyl Peroxide ◽  
Radical Cascade
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