A facile access to N-sulfonylthioimidates and their use for the transformation to 3,4-dihydroquinazolines

2020 ◽  
Vol 18 (43) ◽  
pp. 8881-8885
Author(s):  
Jia-Yu Wu ◽  
Wei-Jr Liao ◽  
Xiu-Yi Lin ◽  
Chien-Fu Liang
Keyword(s):  
Copper Catalyst ◽  
Terminal Alkynes ◽  
Sulfonyl Azide

N-sulfonylthioimidates can be synthesized via terminal alkynes, sulfonyl azide, and thiols using a copper catalyst in the presence of 4-dimethylaminopyridine. Subsequently, it can be transformed to crucial pharmacophores of 3,4-dihydroquinazoline.

Efficient Carboxylation of Terminal Alkynes with Carbon Dioxide Catalyzed by Ligand‐Free Copper Catalyst under Ambient Conditions

2019 ◽  
Vol 8 (8) ◽  
pp. 1501-1505 ◽  
Author(s):  
Wan‐Hui Wang ◽  
Lihong Jia ◽  
Xiujuan Feng ◽  
Dingqiao Fang ◽  
Hongyu Guo ◽  
...  
Keyword(s):  
Carbon Dioxide ◽  
Copper Catalyst ◽  
Terminal Alkynes ◽  
Ambient Conditions ◽  
Ligand Free

scholarly journals One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation

2021 ◽  
Vol 8 ◽  
Author(s):  
Fa-Jie Chen ◽  
Zhenguo Hua ◽  
Jianhui Chen ◽  
Jiajia Chen ◽  
Daesung Lee ◽  
...  
Keyword(s):  
Efficient Method ◽  
Room Temperature ◽  
Copper Catalyst ◽  
High Yield ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Acid Chlorides ◽  
Triflic Acid ◽  
One Pot

Herein, we report an efficient method for the synthesis of (Z)-β-halovinyl ketones through a one-pot Sonogashira coupling and hydrohalogenation reaction promoted by palladium-copper catalyst and Brønsted acid. The ynone intermediates are generated in situ from readily available acid chlorides and terminal alkynes at room temperature, which are directly converted to (Z)-β-halovinyl ketones by treating with triflic acid. This method avoids the use of an external halogen source and features broad substrate scope, high yield, and good to excellent stereoselectivity.

scholarly journals Copper-catalyzed direct transformation of simple alkynes to alkenyl nitriles via aerobic oxidative N-incorporation

2015 ◽  
Vol 6 (11) ◽  
pp. 6355-6360 ◽  
Author(s):  
Xiaoqiang Huang ◽  
Xinyao Li ◽  
Ning Jiao
Keyword(s):  
Late Stage ◽  
Copper Catalyst ◽  
Terminal Alkynes ◽  
Direct Transformation ◽  
N Incorporation

A novel Cu-catalyzed aerobic oxidative N-incorporation into aliphatic terminal alkynes for the synthesis of alkenyl nitriles has been reported. The usage of inexpensive copper catalyst, O2as the sole oxidant, broad substrate scope as well as the feasibility for “the late-stage modification” make this protocol very promising.

Novel Catalytic Three-Component Reaction between a Terminal Alkyne, Sulfonyl Azide, and O-Methyl Oxime

Synlett ◽  
2017 ◽  
Vol 28 (12) ◽  
pp. 1445-1448 ◽  
Author(s):  
Mehdi Khalaj ◽  
Majid Ghazanfarpour-Darjani ◽  
Forugh Barat-Seftejani ◽  
Azita Nouri
Keyword(s):  
Terminal Alkynes ◽  
Terminal Alkyne ◽  
Optimum Conditions ◽  
Three Component Reaction ◽  
Sulfonyl Azides ◽  
Sulfonyl Azide ◽  
Optimized Conditions

O-Methyl oximes have been employed as nucleophiles in reactions with ketenimines derived from sulfonyl azides and terminal alkynes to form N-alkylidene N′-tosylacetimidamide derivatives. The optimized conditions involved the use of CuPF6 and i-Pr2NEt in MeCN at 65 °C. Both O-methyl aldoximes and ketoximes were tolerated under the optimum conditions.

Efficient Ring-Closure Approach via Copper-Catalyzed Reactions of Sulfonyl Azide, Terminal Alkynes and Alcohols/Amines

Synlett ◽  
2007 ◽  
Vol 2007 (6) ◽  
pp. 0901-0904
Author(s):  
Hua Fu ◽  
Ying Jin ◽  
Yingwu Yin ◽  
Yuyang Jiang ◽  
Yufen Zhao
Keyword(s):  
Ring Closure ◽  
Terminal Alkynes ◽  
Sulfonyl Azide ◽  
Catalyzed Reactions

scholarly journals Enantiocontrol by assembled attractive interactions in copper-catalyzed asymmetric direct alkynylation of α-ketoesters with terminal alkynes: OH⋯O/sp3-CH⋯O two-point hydrogen bonding combined with dispersive attractions

2018 ◽  
Vol 9 (14) ◽  
pp. 3484-3493 ◽  
Author(s):  
Martin C. Schwarzer ◽  
Akane Fujioka ◽  
Takaoki Ishii ◽  
Hirohisa Ohmiya ◽  
Seiji Mori ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Copper Catalyst ◽  
Terminal Alkynes

A chiral copper catalyst selects enantiofaces by assembled attractive interactions.

Efficient Ring-Closure Approach via Copper-Catalyzed Reactions of Sulfonyl Azide, Terminal Alkynes and Alcohols/Amines.

ChemInform ◽  
2007 ◽  
Vol 38 (32) ◽  
Author(s):  
Ying Jin ◽  
Hua Fu ◽  
Yingwu Yin ◽  
Yuyang Jiang ◽  
Yufen Zhao
Keyword(s):  
Ring Closure ◽  
Terminal Alkynes ◽  
Sulfonyl Azide ◽  
Catalyzed Reactions

Synthesis of 1,4-Disubstituted 1H-1,2,3-Triazoles from 4-(1-Adamantyl)benzyl Azide through a 1,3-Dipolar Cycloaddition Reaction

Synlett ◽  
2018 ◽  
Vol 29 (20) ◽  
pp. 2685-2688
Author(s):  
Dahmane Tebbani ◽  
Artur Silva ◽  
Oussama Hocine
Keyword(s):  
Copper Catalyst ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Terminal Alkynes ◽  
Triazole Derivatives

A series of new 1,4-disubstituted 1H-1,2,3-triazole derivatives were synthesized by an efficient copper-catalyzed 1,3-dipolar cyclo­addition reaction of 4-(1-adamantyl)benzyl azide with several terminal alkynes. The copper catalyst was used to provide 1,4-disubstituted 1,2,3-triazoles regioselectively in good yields.

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