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.

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.

ChemInform Abstract: Preparation of Nitrogen Heterocycles from Aromatic Amines Using Tris( isopropylthio)cyclopropenyl Cation as a Three-Carbon Building Block.

ChemInform ◽  
2010 ◽  
Vol 23 (35) ◽  
pp. no-no
Author(s):  
H. KOJIMA ◽  
N. MATSUMURA ◽  
H. INOUE
Keyword(s):  
Building Block ◽  
Aromatic Amines ◽  
Nitrogen Heterocycles

Efficient Copper-Catalysed Synthesis of Carbazoles by Double N-Arylation of Primary Amines with 2,2′-Dibromobiphenyl in the Presence of Air

Synlett ◽  
2021 ◽  
Author(s):  
Tran Quang Hung ◽  
Tuan Thanh Dang ◽  
Peter Langer ◽  
Ha Nam Do ◽  
Nguyen Minh Quan ◽  
...  
Keyword(s):  
Aromatic Amines ◽  
Aliphatic Amines ◽  
Primary Amines ◽  
Coupling Reactions ◽  
Carbazole Derivatives ◽  
High Yields

AbstractAn efficient Cu-catalyzed synthesis of carbazole derivatives is reported, which proceeds by double C–N coupling reactions of 2,2′-dibromobiphenyl and amines in the presence of air. The reaction is robust, proceeds in high yields, and tolerates a series of amines including neutral, electron-rich, electron-deficient aromatic amines and aliphatic amines.

Cyclization of 2-(2-bromoethoxy)-acetophenones and 5-(ω-haloalkoxy)-1,5-dihydro-2H-pyrrol-2-ones – Formation of five- to eight-membered oxygen-containing heterocycles via intramolecular alkylation

2004 ◽  
Vol 82 (5) ◽  
pp. 571-578 ◽  
Author(s):  
Kirill V Nikitin ◽  
Nonna P Andryukhova
Keyword(s):  
Sodium Hydride ◽  
Spiro Compounds ◽  
Lithium Diisopropylamide ◽  
Intramolecular Alkylation ◽  
High Yields

Under basic conditions (lithium diisopropylamide or sodium hydride in THF) 2-(2-bromoethoxy)-acetophenones were transformed to 3,4-dihydro[1]benzoxepin-5(2H)-ones (homochromanones) in high yields. The preparation of novel tetrahydropyrano[2,3-b]pyrrol-6(2H)-ones and 3,4-dihydro-2H-pyrrolo[2,1-b][1,3]oxazin-6(8aH)-ones and spiro compounds was performed using similar cyclization in moderate to good yields.Key words: cyclization, lithiation, spiro heterocycles.

Rapid and Green One-Pot Synthesis of Novel 2-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-2-(arylamino)-1H-indene-1,3(2H)-diones

2021 ◽  
Vol 18 ◽  
Author(s):  
Abolfazl Olyaei ◽  
Zahra Ghahremany ◽  
Madieh Sadeghpour
Keyword(s):  
Aromatic Amines ◽  
Low Cost ◽  
Guanidine Hydrochloride ◽  
Reaction Times ◽  
Solvent Free ◽  
One Pot ◽  
Solvent Free Conditions ◽  
The One ◽  
High Yields ◽  
Work Up

: A green and efficient protocol was developed for the one-pot three-component synthesis of novel 2-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-(arylamino)-1H-indene-1,3(2H)-dione derivatives by the reaction of 4-hydroxycoumarin, ninhydrin and aromatic amines in the presence of guanidine hydrochloride as an organocatalyst under solvent-free conditions. The present approach offers several advantages such as low cost, simple work-up, short reaction times, chromatography-free purification, high yields and greener conditions.

UV-Light-Induced Dehydrogenative N-Acylation of Amines with 2-Nitrobenzaldehydes to Give 2-Aminobenzamides

Synthesis ◽  
2022 ◽  
Author(s):  
Dishu Zeng ◽  
Tianbao Yang ◽  
Niu Tang ◽  
Wei Deng ◽  
Jiannan Xiang ◽  
...  
Keyword(s):  
Amino Acid ◽  
Organic Synthesis ◽  
Efficient Method ◽  
Building Block ◽  
Room Temperature ◽  
Uv Light ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Plausible Mechanism ◽  
High Yields

A simple, mild, green and efficient method for the synthesis of 2-aminobenzamides was highly desired in organic synthesis. Herein, we developed an efficient, one-pot strategy for the synthesis of 2-aminobenzamides with high yields irradiated by UV light. 32 examples proceeded successfully by this photo-induced protocol. The yield reached up to 92%. The gram scale was also achieved easily. This building block could be applied in the preparation of quinazolinones derivatives. Amino acid derivatives could be employed smoothly at room temperature. Finally, a plausible mechanism was proposed.

Isopropyl N-Arylmalonamates. Synthesis, Structure, Conformation and Reactions with Carbon Disulfide

2006 ◽  
Vol 71 (1) ◽  
pp. 59-76 ◽  
Author(s):  
Wolf-Dieter Rudorf ◽  
Dušan Loos ◽  
Joanna Wybraniec ◽  
Naďa Prónayová ◽  
Ryszard Gawinecki ◽  
...  
Keyword(s):  
Molecular Structure ◽  
Hydrogen Bonding ◽  
Carbon Disulfide ◽  
Aromatic Amines ◽  
Alkylating Agent ◽  
Sodium Hydride ◽  
Open Chain ◽  
Ketene Dithioacetals ◽  
Correlation Analyses ◽  
C Nmr

Acylation of aromatic amines 1 with diisopropyl malonate (2) leads to a mixture of isopropyl N-arylmalonamates 3 and malonanilides 4. The reaction of 3 with carbon disulfide in the presence of sodium hydride gives disodium salts 5. Treatment of 5 with an alkylating agent yields the open-chain or cyclic ketene dithioacetals 6, 7 or 8. The molecular structure, hydrogen bonding and preferential conformation of the isopropyl N-arylmalonamates 3, 6 and 7 were investigated using correlation analyses of IR, 13C NMR and AM1 semiempirical data.

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.

scholarly journals Microwave assisted synthesis of five membered nitrogen heterocycles

RSC Advances ◽  
2020 ◽  
Vol 10 (59) ◽  
pp. 36031-36041
Author(s):  
Gopinadh Meera ◽  
K. R. Rohit ◽  
Salim Saranya ◽  
Gopinathan Anilkumar
Keyword(s):  
Reaction Time ◽  
Nitrogen Heterocycles ◽  
Product Formation ◽  
Microwave Assisted Synthesis ◽  
Short Reaction Time ◽  
Microwave Assisted ◽  
High Yields

Microwave assisted synthesis of N-heterocycles with short reaction time, high yields and high product purities along with a decrease in the rate of by-product formation.

The Reactions of Dmso with Arylaldehydes in the Presence of Sodium Hydride

2002 ◽  
Vol 2002 (9) ◽  
pp. 422-427 ◽  
Author(s):  
Min Shi ◽  
Yu-Mei Shen
Keyword(s):  
Dimethyl Sulfoxide ◽  
Sodium Hydride

Dimethyl sulfoxide (DMSO) reacted with arylaldehydes under basic conditions to afford sulfide 1, β-(benzyloxy)styrene 2 and dialkyl sulfoxide 3, while the reaction of benzophenone with DMSO gave 1,1-diphenylethylene 4, 1,1-diphenyl-2-methylthioethylene 5 and sulfoxide 6 at the same time under the same conditions.

Sign in / Sign up

Export Citation Format

Share Document