Phosphine-catalyzed [4 + 3] cycloaddition reaction of aromatic azomethine imines with allenoates

RSC Advances ◽  
2015 ◽  
Vol 5 (43) ◽  
pp. 34481-34485 ◽  
Author(s):  
Zhen Li ◽  
Hao Yu ◽  
Yalin Feng ◽  
Zhanfeng Hou ◽  
Lei Zhang ◽  
...  
Keyword(s):  
Heterocyclic Compounds ◽  
Cycloaddition Reaction ◽  
Azomethine Imines

An efficient phosphine-catalyzed [4 + 3] cycloaddition of aromatic azomethine imines with allenoates has been developed, providing dinitrogen-fused heterocyclic compounds in moderate to excellent yields.

Polar Diels-Alder Reactions Under Microwave Irradiation Employing Different Heterocyclic Compounds as Electrophiles

2019 ◽  
Vol 16 (6) ◽  
pp. 527-543 ◽  
Author(s):  
Pedro M.E. Mancini ◽  
Carla M. Ormachea ◽  
María N. Kneeteman
Keyword(s):  
Organic Synthesis ◽  
Heterocyclic Compounds ◽  
Ionic Conduction ◽  
Theoretical Calculations ◽  
Cycloaddition Reaction ◽  
Diels Alder ◽  
The Other ◽  
Conventional Heating ◽  
Protic Ionic Liquids ◽  
Solvent Free Conditions

During the last twenty years, our research group has been working with aromatic nitrosubstituted compounds acting as electrophiles in Polar Diels-Alder (P-DA) reactions with different dienes of diverse nucleophilicity. In this type of reaction, after the cycloaddition reaction, the nitrated compounds obtained as the [4+2] cycloadducts suffer cis-extrusion with the loss of nitrous acid and a subsequent aromatization. In this form, the reaction results are irreversible. On the other hand, the microwave-assisted controlled heating become a powerful tool in organic synthesis as it makes the reaction mixture undergo heating by a combination of thermal effects, dipolar polarization and ionic conduction. As the Diels-Alder (D-A) reaction is one of the most important process in organic synthesis, the microwave (MW) irradiation was applied instead of conventional heating, and this resulted in better yields and shorter reaction times. Several substituted heterocyclic compounds were used as electrophiles and different dienes as nucleophiles. Two experimental situations are involved: one in the presence of Protic Ionic Liquids (PILs) as solvent and the other under solvent-free conditions. The analysis is based on experimental data and theoretical calculations.

scholarly journals Synthesis and biological activity of 4-thiazolidinone derivatives of phenothiazine

2012 ◽  
Vol 77 (1) ◽  
pp. 17-26 ◽  
Author(s):  
Ritu Sharma ◽  
Pushkal Samadhiya ◽  
Savitri Srivastava ◽  
Santosh Srivastava
Keyword(s):  
Antimicrobial Activity ◽  
Heterocyclic Compounds ◽  
Thioglycolic Acid ◽  
Cycloaddition Reaction ◽  
Aromatic Aldehydes ◽  
Knoevenagel Reaction ◽  
Antituberculosis Activity ◽  
Bacteria And Fungi ◽  
Derivatives Of ◽  
Anhydrous Zncl2

A new series of N-[3-(10H-phenothiazinyl)-propyl]-2-(substituted phenyl)-4-oxo-5-( substituted benzylidene)-1,3-thiazolidine-carboxamide, 5(as) have been synthesized. The cycloaddition reaction of thioglycolic acid with N-[3-(10H-phenothiazinyl)-propyl]-N?-[(substituted phenyl)-methylidene]- urea, 3(a-s) in the presence of anhydrous ZnCl2 afforded new heterocyclic compounds N-[3-(10H-phenothiazinyl)-propyl]-2-(substituted phenyl)-4-oxo- 1,3-thiazolidine-carboxamide, 4(a-s). The later product on treatment with several selected substituted aromatic aldehydes in the presence of C2H5ONa undergoes Knoevenagel reaction to yield 5(a-s). The structure of compounds 1, 2, 3(a-s), 4(a-s) and 5(a-s) were confirmed by IR, 1H NMR, 13C NMR, Fmass and chemical analysis. All above compounds were screened for their antimicrobial activity against some selected bacteria and fungi and for antituberculosis activity compounds have been screened against the bacterium M. tuberculosis.

scholarly journals 1,3-Dipolar cycloaddition of isatin N,N′-cyclic azomethine imines with α,β-unsaturated aldehydes catalyzed by DBU in water

RSC Advances ◽  
2020 ◽  
Vol 10 (41) ◽  
pp. 24288-24292 ◽  
Author(s):  
Zhan-Yong Wang ◽  
Ting Yang ◽  
Rongxiang Chen ◽  
Xueji Ma ◽  
Huan Liu ◽  
...  
Keyword(s):  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Unsaturated Aldehydes ◽  
Quaternary Center ◽  
Azomethine Imines ◽  
Green Procedure

A simple and green procedure was established by [3 + 3] cycloaddition reaction of isatin derived cyclic imine 1,3-dipoles with α,β-unsaturated aldehydes, giving spirooxindoles with aza-quaternary center in good yields and diastereoselectivities.

B(C6F5)3-Catalyzed cyclization of alkynes: direct synthesis of 3-silyl heterocyclic compounds

2020 ◽  
Vol 56 (80) ◽  
pp. 11953-11956
Author(s):  
Mengxing Li ◽  
Ting Wang ◽  
Zhenyu An ◽  
Rulong Yan
Keyword(s):  
Heterocyclic Compounds ◽  
Direct Synthesis ◽  
Cycloaddition Reaction ◽  
Easy Access ◽  
One Pot

An efficient one-pot strategy for easy access to 3-silyl heterocyclic compounds was developed via a B(C6F5)3-catalyzed cycloaddition reaction of o-(1-alkynyl)(thio)anisoles or o-(1-alkynyl)-N-methylaniline.

Highly stereoselective [3+2]-cycloaddition reaction of stabilised N , N ′-cyclic azomethine imines with 3-nitro-2-phenyl-2 H -chromenes: Synthesis of tetrahydrochromeno[4,3- c ]pyrazolo[1,2- a ]pyrazol-11-ones

2017 ◽  
Vol 58 (42) ◽  
pp. 3989-3992 ◽  
Author(s):  
Alexey Y. Barkov ◽  
Nikolay S. Zimnitskiy ◽  
Igor B. Kutyashev ◽  
Vladislav Y. Korotaev ◽  
Vyacheslav Y. Sosnovskikh
Keyword(s):  
Cycloaddition Reaction ◽  
Azomethine Imines

Chiral NHC-catalyzed 1,3-dipolar [3 + 2] cycloaddition of azomethine imines with α-chloroaldehydes for the synthesis of bicyclic pyrazolidinones

2018 ◽  
Vol 16 (24) ◽  
pp. 4433-4438 ◽  
Author(s):  
Limin Yang ◽  
Yunbo Lv ◽  
Fei Wang ◽  
Guofu Zhong
Keyword(s):  
Cycloaddition Reaction ◽  
Azomethine Imines

An NHC-catalyzed [3 + 2] cycloaddition reaction of azomethine imines and α-chloroaldehydes was developed for the synthesis of chiral bicyclic pyrazolidinone derivatives.

Sign in / Sign up

Export Citation Format

Share Document