Intramolecular Cyclization of Azides by Iminium Species. A Novel Method for the Construction of Nitrogen Heterocycles under Vilsmeier Conditions

1998 ◽  
Vol 63 (21) ◽  
pp. 7136-7142 ◽  
Author(s):  
Vattoly J. Majo ◽  
Paramasivan T. Perumal
Keyword(s):  
Intramolecular Cyclization ◽  
Nitrogen Heterocycles ◽  
Novel Method

scholarly journals A Synthesis of 4-Chloro-2-(trichloromethyl)pyrimidines and Their Study in Nucleophilic Substitution

Synthesis ◽  
2018 ◽  
Vol 51 (02) ◽  
pp. 530-537 ◽  
Author(s):  
Moisés Romero-Ortega ◽  
Michelle Trujillo-Lagunas ◽  
Ignacio Medina-Mercado ◽  
Ivann Zaragoza-Galicia ◽  
Horacio Olivo
Keyword(s):  
Nucleophilic Substitution ◽  
Intramolecular Cyclization ◽  
Nitrogen Heterocycles ◽  
Cyclization Reaction ◽  
Substitution Reactions ◽  
Pyrimidine Derivatives ◽  
One Pot ◽  
Acyl Chlorides ◽  
Nucleophilic Substitution Reactions ◽  
One Pot Synthesis

A convenient two-step, one-pot synthesis of 4-chloro-2-(trichloromethyl)pyrimidines starting from 2-(trichloromethyl)-1,3-diazabutadienes is described. These nitrogen heterocycles were prepared by a sequential acylation/intramolecular cyclization reaction between 2-(trichloromethyl)-1,3-diazabutadienes and acyl chlorides in the presence of triethylamine followed by treatment with POCl3. This is the first report for the synthesis of this type of 4-chloro-2-(trichloromethyl)pyrimidine derivatives and serves as a source for a wide variety of other substituted pyrimidines by nucleophilic substitution reactions.

Synthesis of Nitrogen Heterocycles by Intramolecular Cyclization of Alkenyl N-Acylaminophthalimides Using Phenyliodine(III) Bis(trifluoroacetate) (PIFA)

Heterocycles ◽  
2008 ◽  
Vol 75 (5) ◽  
pp. 1133 ◽  
Author(s):  
Yasuo Kikugawa ◽  
Masato Tsukamoto ◽  
Kousuke Murata ◽  
Takeshi Sakamoto ◽  
Setsuo Saito
Keyword(s):  
Intramolecular Cyclization ◽  
Nitrogen Heterocycles

Studies on Instructive Construction of exo-Olefin Terminated Five- and Six-Membered Nitrogen Heterocycles: SmI2-Mediated Intramolecular Cyclization of Haloalkynals

2018 ◽  
Vol 83 (17) ◽  
pp. 10636-10645 ◽  
Author(s):  
Kazunori Takahashi ◽  
Kei Fukushima ◽  
Marina Seto ◽  
Azusa Togashi ◽  
Yuichi Arai ◽  
...  
Keyword(s):  
Intramolecular Cyclization ◽  
Nitrogen Heterocycles

Preparation of nitrogen heterocycles from aromatic amines using tris(isopropylthio)cyclopropenyl cation as a three-carbon building block

1992 ◽  
Vol 70 (1) ◽  
pp. 1-4 ◽  
Author(s):  
Hideo Kojima ◽  
Noboru Matsumura ◽  
Hiroo Inoue
Keyword(s):  
Dimethyl Sulfoxide ◽  
Intramolecular Cyclization ◽  
Building Block ◽  
Aromatic Amines ◽  
Nitrogen Heterocycles ◽  
Sodium Hydride ◽  
Iminium Salts ◽  
High Yields

Quinolines (2 and 3) and naphthazepines (8 and 9) are prepared in high yields by the reaction of tris(isopropylthio)-cyclopropenylium perchlorate (1) with anilines and 1-naphthylamines, respectively, under nitrogen in N,N-dimethylformamide at 80–85 °C. The reactions are proven to proceed through the intermediary formation of iminium salts (5, 10, and 11) derived from 1 and amines. The reaction of 1 with pyrrole and indole in dimethyl sulfoxide, containing sodium hydride, at 25 °C gives 5,6,7-tris(isopropylthio)-1H-pyrrolizine (12) and 1,2,3-tris(isopropylthio)-9H-fluorazene (14), respectively, in high yields by intramolecular cyclization of a vinylcarbene intermediate. The possible pathway for the formation of these nitrogen heterocycles is proposed. Keywords: cyclopropenyl cation, aromatic amines, nitrogen heterocycles, three-carbon building block.

Mass spectrometry of nitrogen heterocycles. 3. Thermal intramolecular cyclization of 2-azolylaminopyridines

1991 ◽  
Vol 27 (1) ◽  
pp. 84-88
Author(s):  
V. L. Rusinov ◽  
N. A. Klyuev ◽  
V. G. Baklykov ◽  
T. L. Pilicheva ◽  
A. A. Tumashov
Keyword(s):  
Mass Spectrometry ◽  
Intramolecular Cyclization ◽  
Nitrogen Heterocycles
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