Multiple-functionalizations of terminal alkynes with sodium sulfinates and tert-butyl nitrite: facile synthesis of 2H-azirines

2019 ◽  
Vol 55 (24) ◽  
pp. 3517-3520 ◽  
Author(s):  
Xingyi He ◽  
Xin Yue ◽  
Lei Zhang ◽  
Shuang Wu ◽  
Ming Hu ◽  
...  

A new, catalyst-free tandem annulation route to 2,2-disulfonyl-2H-azirines via multiple-functionalizations of terminal alkynes with sodium sulfinates and tert-butyl nitrite is described.

2012 ◽  
Vol 90 (5) ◽  
pp. 450-463 ◽  
Author(s):  
David I. Magee ◽  
Same Ratshonka ◽  
Jessica McConaghy ◽  
Maggie Hood

The synthesis of a large number of β- and β,β-substituted keto esters was successful by the use of the Knoevenagel condensation reaction. The stereoselectivity of these reactions was improved by alteration of various substituent groups. Although there were few examples of complete Z selectivity, the use of tert-butyl acetoacetate with either aromatic or aliphatic aldehydes afforded Z selectivity. The selective reductions of these substituted keto esters was successfully achieved by using a combination of NaBH4 and CeCl3·7H2O or Yb(OTf)3, which allowed a facile synthesis of a large number of stereochemically pure substituted Morita–Baylis–Hillman adducts, including β,β-substituted adducts.


Synthesis ◽  
2015 ◽  
Vol 48 (01) ◽  
pp. 122-130 ◽  
Author(s):  
Hua Wang ◽  
Daoshan Yang ◽  
Kelu Yan ◽  
Wei Wei ◽  
Yao Liu ◽  
...  

1993 ◽  
Vol 34 (46) ◽  
pp. 7409-7412 ◽  
Author(s):  
Pierre Chevallet ◽  
Patrick Garrouste ◽  
Barbara Malawska ◽  
Jean Martinez

2020 ◽  
Vol 16 ◽  
pp. 1683-1692 ◽  
Author(s):  
Dominik Göbel ◽  
Marius Friedrich ◽  
Enno Lork ◽  
Boris J Nachtsheim

Herein, we present a facile synthesis of three azide-functionalized fluorophores and their covalent attachment as triazoles in Huisgen-type cycloadditions with model alkynes. Besides two ortho- and para-bromo-substituted benzaldehydes, the azide functionalization of a fluorene-based structure will be presented. The copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) of the so-synthesized azide-functionalized bromocarbaldehydes with terminal alkynes, exhibiting different degrees of steric demand, was performed in high efficiency. Finally, we investigated the photophysical properties of the azide-functionalized arenes and their covalently linked triazole derivatives to gain deeper insight towards the effect of these covalent linkers on the emission behavior.


2019 ◽  
Vol 38 (1) ◽  
pp. 17-23 ◽  
Author(s):  
Wei-Wen Chi ◽  
Rong-Yuan Zhang ◽  
Ting Han ◽  
Jian Du ◽  
Hong-Kun Li ◽  
...  

ChemInform ◽  
2001 ◽  
Vol 32 (3) ◽  
pp. no-no
Author(s):  
Takashi Ooi ◽  
Minoru Kameda ◽  
Hidenori Tannai ◽  
Keiji Maruoka

2019 ◽  
Vol 17 (35) ◽  
pp. 8153-8165 ◽  
Author(s):  
Jitendra Gour ◽  
Srikanth Gatadi ◽  
Ravikumar Akunuri ◽  
Madhavi Venkata Yaddanapudi ◽  
Mushtaq Ahmad Nengroo ◽  
...  

A general and catalyst-free access to the fused polycyclic N-heterocycles via an intramolecular azide–alkene cascade reaction under mild reaction conditions has been developed.


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