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

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.

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

Synthesis of nitrogen heterocycles via palladium-catalyzed intramolecular cyclization

1987 ◽  
Vol 28 (44) ◽  
pp. 5291-5294 ◽  
Author(s):  
Richard C. Larock ◽  
Srinivasan Babu
Keyword(s):  
Intramolecular Cyclization ◽  
Nitrogen Heterocycles ◽  
Palladium Catalyzed

Potassium Periodate Mediated Oxidative Cyclodesulfurization toward Benzofused Nitrogen Heterocycles

Synthesis ◽  
2020 ◽  
Vol 52 (13) ◽  
pp. 1981-1990
Author(s):  
Mookda Pattarawarapan ◽  
Chuthamat Duangkamol ◽  
Wong Phakhodee
Keyword(s):  
Intramolecular Cyclization ◽  
Oxidative Coupling ◽  
Nitrogen Heterocycles ◽  
Coupling Reactions ◽  
Substituted Anilines ◽  
Potassium Periodate ◽  
High Yields ◽  
Quinazolinone Derivatives ◽  
Oxidative Coupling Reactions

A convenient oxidative cyclodesulfurization method toward the synthesis of benzofused nitrogen heterocycles using inexpensive and readily available potassium periodate as an oxidant was developed. Upon treating isothiocyanates with ortho-substituted anilines bearing N,N-, N,O-, and N,S-bis-nucleophiles, followed by an intramolecular cyclization of the in situ generated monothioureas, substituted 2-aminobenzazole series were rapidly accessible in good to excellent yields. The protocol can accommodate various substituents on both substrates while allowing more efficient, greener, and operational simpler process relative to other oxidative coupling reactions. Tetracyclic quinazolinone derivatives were also afforded in high yields in a single preparative step and chromatography-free.

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