In situ generation and protonation of the isocyanide/acetylene adduct: a powerful catalyst-free strategy for multicomponent synthesis of ketenimines, aza-dienes, and heterocycles

RSC Advances ◽  
2015 ◽  
Vol 5 (117) ◽  
pp. 97044-97065 ◽  
Author(s):  
Sadegh Rostamnia
Keyword(s):  
Multicomponent Reactions ◽  
Multicomponent Synthesis ◽  
New Class ◽  
Catalyst Free ◽  
In Situ Generation

In addition to isocyanide-based Ugi, Passerini, van Leusen, and Orru multicomponent reactions, a new class of isocyanide/acetylene-based multicomponent reactions, using zwitterionic adducts, have emerged as powerful methods to synthesize biologically interesting molecules.

scholarly journals Facile Synthesis of Chrysin-derivatives with Promising Activities as Aromatase Inhibitors†

2011 ◽  
Vol 6 (1) ◽  
pp. 1934578X1100600 ◽  
Author(s):  
Hamdoon A. Mohammed ◽  
Lalla A. Ba ◽  
Torsten Burkholz ◽  
Elena Schumann ◽  
Britta Diesel ◽  
...  
Keyword(s):  
Aromatase Inhibitors ◽  
Anticancer Agents ◽  
Multicomponent Reactions ◽  
Multicomponent Synthesis ◽  
Facile Synthesis ◽  
Functional Elements ◽  
Lead Structure ◽  
New Class ◽  
Flavone Derivatives ◽  
Human Aromatase

Flavones such as chrysin show structural similarities to androgens, the substrates of human aromatase, which converts androgens to estrogens. Aromatase is a key target in the treatment of hormone-dependent tumors, including breast cancer. Flavone-based aromatase inhibitors are of growing interest, and chrysin in particular provides a (natural) lead structure. This paper reports multicomponent synthesis as a means for facile modification of the chrysin core structure in order to add functional elements. A Mannich-type reaction was used to synthesize a range of mono- and disubstituted chrysin derivatives, some of which are more effective aromatase inhibitors than the benchmark compound, aminoglutethimide. Similarly, the reaction of chrysin with various isonitriles and acetylene dicarboxylates results in a new class of flavone derivatives, tricyclic pyrano-flavones which also inhibit human aromatase. Multicomponent reactions involving flavones therefore enable the synthesis of a variety of derivatives, some of which may be useful as anticancer agents.

scholarly journals Diastereoselective Synthesis of some pyrrolidin-2-ones azasugars and study of their stereochemistry

2019 ◽  
Vol 8 (1) ◽  
pp. 42-52 ◽  
Author(s):  
Chahrazed Benhaoua ◽  
Mustapha Rahmouni ◽  
Hadj Benhaoua
Keyword(s):  
Reaction Times ◽  
Diastereoselective Synthesis ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
Cyanide Group ◽  
Iminium Ions ◽  
In Situ Generation ◽  
Work Up ◽  
Reaction Profile

The microwave-promoted one-pot multicomponent synthesis of substituted pyrrolidinols using a bifunctional sugar-derived hydroxy-[gamma]-lactone component of amine component or cyanide group is reported. Clean reaction profile, easy work-up procedure, excellent yields and short reaction times are some remarkable features of this method.This modular approach features the in situ-generation of iminium ions intermediate that allows the diastereoselective assembly of the diverse pyrrolidinones efficiently under microwave irradiation has been used.

scholarly journals Synthesis and selected transformations of 2-unsubstituted 1-(adamantyloxy)imidazole 3-oxides: straightforward access to non-symmetric 1,3-dialkoxyimidazolium salts

2019 ◽  
Vol 15 ◽  
pp. 497-505 ◽  
Author(s):  
Grzegorz Mlostoń ◽  
Małgorzata Celeda ◽  
Katarzyna Urbaniak ◽  
Marcin Jasiński ◽  
Vladyslav Bakhonsky ◽  
...  
Keyword(s):  
Hydrobromic Acid ◽  
Room Temperature ◽  
Elemental Sulfur ◽  
Acid Anhydride ◽  
Monomeric Form ◽  
New Class ◽  
Raney Ni ◽  
In Situ Generation ◽  
Alkylation Reactions

Adamantyloxyamine reacts with formaldehyde to give N-(adamantyloxy)formaldimine as a room-temperature-stable compound that exists in solution in monomeric form. This product was used for reactions with α-hydroxyiminoketones leading to a new class of 2-unsubstituted imidazole 3-oxides bearing the adamantyloxy substituent at N(1). Their reactions with 2,2,4,4-tetramethylcyclobutane-1,3-dithione or with acetic acid anhydride occurred analogously to those of 1-alkylimidazole 3-oxides to give imidazol-2-thiones and imidazol-2-ones, respectively. Treatment of 1-(adamantyloxy)imidazole 3-oxides with Raney-Ni afforded the corresponding imidazole derivatives without cleavage of the N(1)–O bond. Finally, the O-alkylation reactions of the new imidazole N-oxides with 1-bromopentane or 1-bromododecane open access to diversely substituted, non-symmetric 1,3-dialkoxyimidazolium salts. Adamantyloxyamine reacts with glyoxal and formaldehyde in the presence of hydrobromic acid yielding symmetric 1,3-di(adamantyloxy)-1H-imidazolium bromide in good yield. Deprotonation of the latter with triethylamine in the presence of elemental sulfur allows the in situ generation of the corresponding imidazol-2-ylidene, which traps elemental sulfur yielding a 1,3-dihydro-2H-imidazole-2-thione as the final product.

Highly diastereo- and enantioselective organocatalytic synthesis of trifluoromethylated erythritols based on the in situ generation of unstable trifluoroacetaldehyde

2021 ◽  
Author(s):  
Kazumasa Funabiki ◽  
Toshiya Gotoh ◽  
Ryunosuke Kani ◽  
Toshiyasu Inuzuka ◽  
Yasuhiro Kubota
Keyword(s):  
Trifluoromethyl Group ◽  
In Situ Generation

A highly diastereo- and enantioselective organocatalytic method to synthesise erythritols bearing a trifluoromethyl group has been investigated.

Recent advances in Minisci-type reactions and applications in organic synthesis

2020 ◽  
Vol 24 ◽  
Author(s):  
Wengui Wang ◽  
Shoufeng Wang
Keyword(s):  
Free Radical ◽  
Hydrogen Atom ◽  
Organic Synthesis ◽  
Radical Reactivity ◽  
Atom Loss ◽  
Radical Generation ◽  
In Situ Generation ◽  
Thermal Cleavage ◽  
Synthetic Chemist

Abstract:: Minisci-type reactions have become widely known as reactions that involve the addition of carbon-centered radicals to basic heteroarenes followed by formal hydrogen atom loss. While the originally developed protocols for radical generation remain in active use today, in recent years by a new array of radical generation strategies allow use of a wider variety of radical precursors that often operate under milder and more benign conditions. New transformations based on free radical reactivity are now available to a synthetic chemist looking to utilize a Minisci-type reaction. Radical-generation methods based on photoredox catalysis and electrochemistry, which utilize thermal cleavage or the in situ generation of reactive radical precursors, have become popular approaches. Our review will cover the remarkably literature that has appeared on this topic in recent 5 years, from 2015-01 to 2020-01, in an attempt to provide guidance to the synthetic chemist, on both the challenges that have been overcome and applications in organic synthesis.

Facile and Efficient Synthesis of New Class of Imidazole Derivatives via One-Pot Multicomponent Reactions in Water

2013 ◽  
Vol 16 (10) ◽  
pp. 788-790
Author(s):  
Zinatossadat Hossaini ◽  
Samereh Seyfi ◽  
Faramarz Rostami-Charati ◽  
Mehdi Ghambarian
Keyword(s):  
Multicomponent Reactions ◽  
Efficient Synthesis ◽  
One Pot ◽  
Imidazole Derivatives ◽  
New Class

scholarly journals A residue-free approach to water disinfection using catalytic in situ generation of reactive oxygen species

2021 ◽  
Author(s):  
Thomas Richards ◽  
Jonathan H. Harrhy ◽  
Richard J. Lewis ◽  
Alexander G. R. Howe ◽  
Grzegorz M. Suldecki ◽  
...  
Keyword(s):  
Reactive Oxygen Species ◽  
Reactive Oxygen ◽  
Water Disinfection ◽  
Oxygen Species ◽  
In Situ Generation
Sign in / Sign up

Export Citation Format

Share Document