A metal-free one-pot synthesis of benzo[c]chromen-6-ones from 3,4-dichlorocoumarins and butadienes using tandem photo-thermal-photo reactions

2016 ◽  
Vol 14 (41) ◽  
pp. 9874-9882 ◽  
Author(s):  
Yan Zhang ◽  
Yan Tian ◽  
Pei Xiang ◽  
Ning Huang ◽  
Jianyi Wang ◽  
...  

A concise one-pot synthesis of benzo[c]chromen-6-ones from dichlorocoumarins and butadienes has been achieved, using a photo-initiated formal Diels–Alder reaction, with high overall yields.

2020 ◽  
Author(s):  
Haruyasu Asahara ◽  
Minami Hiraishi ◽  
Nagatoshi Nishiwaki

β-Nitrostyrenes underwent the Diels-Alder reaction with Danishefsky’s diene to afford cyclohexenes together with the corresponding hydrolyzed products, 3-arylated 5-methoxy-4-nitrocyclohexanones. When the reaction was conducted in the presence of water, the cyclohexenes were efficiently hydrolyzed into cyclohexanones. Subsequent aromatization by heating the cyclohexanone with a catalytic amount of iodine in dimethyl sulfoxide gave 3-arylated 4-nitrophenols. The reaction of nitrostyrenes with Danishefsky’s diene could be conducted in one-pot to directly afford the corresponding nitrophenols. Moreover, a heteroaryl group such as a thienyl group could be introduced into the nitrophenol framework.


ChemInform ◽  
2007 ◽  
Vol 38 (14) ◽  
Author(s):  
Kiyosei Takasu ◽  
Naoya Shindoh ◽  
Hidetoshi Takuyama ◽  
Masataka Ihara

2020 ◽  
Vol 16 ◽  
pp. 1830-1836
Author(s):  
Haruyasu Asahara ◽  
Minami Hiraishi ◽  
Nagatoshi Nishiwaki

β-Nitrostyrenes underwent a Diels–Alder reaction with Danishefsky’s diene to afford cyclohexenes together with the corresponding hydrolyzed products, 3-arylated-5-methoxy-4-nitrocyclohexanones. When the reaction was conducted in the presence of water, the cyclohexenes were efficiently hydrolyzed into cyclohexanones. Subsequent aromatization by heating the cyclohexanone with a catalytic amount of iodine in dimethyl sulfoxide gave 3-arylated-4-nitrophenols. The reaction of nitrostyrenes with Danishefsky’s diene could be conducted in one pot to directly afford the corresponding nitrophenols. Moreover, a heteroaryl group, e.g., a thienyl group could be introduced into the nitrophenol framework.


2010 ◽  
Vol 6 (1) ◽  
pp. 884-890
Author(s):  
Raad Kasim Yahya ◽  
K. M. Lokanatha Rai ◽  
Ebraheem Abdu Musad ◽  
P. T. Sowmya

A new series of 5,6-dihydro-4H-1,2-oxazines were synthesized via hetero Diels-Alder reaction of  α-nitrosolefins with derivatives of allylbenzene. α-Nitrosoolefins were generated from ketoximes by the action of chloramine-T and triethylamine.


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