Domino reaction of cyclic sulfamidate imines with Morita–Baylis–Hillman acetates promoted by DABCO: a metal-free approach to functionalized nicotinic acid derivatives

2017 ◽  
Vol 15 (15) ◽  
pp. 3286-3297 ◽  
Author(s):  
Debashis Majee ◽  
Soumen Biswas ◽  
Shaikh M. Mobin ◽  
Sampak Samanta

A series of 4,6-diarylnicotinates have been prepared in good to excellent yields via a domino reaction of cyclic sulfamidate imines with MBH acetates in 2-MeTHF promoted by DABCO under an O2 atmosphere.

2021 ◽  
Author(s):  
Penghui Dong ◽  
Kashif Majeed ◽  
lingna Wang ◽  
Zijian Guo ◽  
Fengtao Zhou ◽  
...  

A transition metal-free aldol condensation/[1+2+3] annulation reaction of isocyanoacetates with 8-(alkynyl)-1-naphthaldehydes has been developed for the general synthesis of azafluoranthenes. This domino reaction enables successive formation of three new bonds...


1940 ◽  
Vol 136 (3) ◽  
pp. 729-745
Author(s):  
William A. Perlzweig ◽  
Edward D. Levy ◽  
Herbert P. Sarett

ChemInform ◽  
1990 ◽  
Vol 21 (43) ◽  
Author(s):  
A. R. KATRITZKY ◽  
G. P. SAVAGE ◽  
M. PILARSKA ◽  
N. S. BODOR ◽  
M. E. BREWSTER

1955 ◽  
Vol 101 (425) ◽  
pp. 884-889 ◽  
Author(s):  
R. Rodnight ◽  
H. Mcilwain

Pellagra with marked mental symptoms in a boy of 10, was cured by nicotinamide (Hersov, 1955). The boy's diet prior to development of the pellagra did not however appear to have been deficient in nicotinic acid derivatives. The following studies were initiated in search for a metabolic peculiarity which might explain this.


2021 ◽  
Author(s):  
Benedikt Grau ◽  
Maximilian Dill ◽  
Frank Hampel ◽  
Axel Kahnt ◽  
Norbert Jux ◽  
...  

Hexaarylbenzene (HAB) derivatives are versatile aromatic systems playing a significant role as chromophores, liquid crystalline materials, molecular receptors, redox materials, organic light-emitting diodes and photochemical switches. Statistical synthesis of simple symmetrical HABs is known <i>via</i> low-yielding cyclotrimerization or Diels-Alder reactions. By contrast, the synthesis of more complex, asymmetrical systems, and without involvement of statistical steps, remains an unsolved problem. Here we present a generally applicable synthetic strategy to access asymmetrical HAB <i>via</i> an atom-economical and high-yielding metal-free four-step domino reaction using nitrostyrenes and <i>α,α</i>-dicyanoolefins as easily available starting materials. Resulting domino product – functionalized triarylbenzene (TAB) - can be used as a key starting compound to furnish asymmetrically substituted hexaarylbenzenes in high overall yield and without involvement of statistical steps. This straightforward domino process represents a distinct approach to creating diverse and still unexplored HAB scaffolds, containing six different aromatic rings around central benzene core.


1997 ◽  
Vol 46 (5) ◽  
pp. 902-905
Author(s):  
E. N. Makareyeva ◽  
Yu. V. Makedonov ◽  
E. L. Lozovskaya

Synthesis ◽  
2020 ◽  
Vol 52 (16) ◽  
pp. 2395-2409
Author(s):  
Weiwei Qin ◽  
Zhaodong Li ◽  
Yiming Du ◽  
Yue Chen ◽  
Yun-Lin Liu

An efficient, PhI(OAc)2-mediated, radical azidoheteroarylation of alkenes under transition-metal-free conditions is reported by employing TMSN3 and quinoxalin-2(1H)-ones as coupling partners. This domino reaction allows an efficient synthesis of valuable orangoazides containing quinoxalin-2(1H)-one derivatives and could be extended to phosphinyl-alkylated quinoxalin-2(1H)-one in a single step in moderate to excellent yields under mild conditions, as demonstrated by the preliminary antibacterial evaluation against Magnaporthe grisea for the first time. Mechanistic studies revealed that this transformation undergoes a cascade addition pathway controlled by a polar radical.


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