Current Organic Synthesis - Volume 10, Issue 5, 2013

Spiroisoxazolines of natural and synthetic origin are of recurring interest to researchers engaged in the areas of natural product synthesis and methodology. The spiroisoxazoline motif is a ubiquitous feature for a number of marine natural products of the order Verongida and display an array of interesting properties ranging from central nervous system (CNS) to antitumor and antifungal effects. Many of these natural pr Read More

Alkylboronate derivatives are important intermediates in organic synthesis and medicinal chemistry. The research of synthesizing alkylboronic acid derivatives has attracted great attention of chemists and many papers have reported various methods for preparing alkylboronates based on transition-metal-catalyzed hydroboration. In this review, we summarize the methods of synthesizing alkylboronate derivatives with differ Read More

The use of ZnO is a topic of continuing interest due to numerous applications in many areas of the chemical industry. In addition, with the development of industrialization, organic chemists have been confronted with a new challenge of finding novel methods in organic synthesis that can reduce and finally eliminate the impact of volatile organic solvents and hazardous toxic chemicals in the environment. Due to this, g Read More

Fullerenes are fascinating carbon molecules that attract an increasing attention due to their interesting properties and possibilities of application. For these applications fullerenes need to be connected to the macroscopic world via their exterior. Hence, the modification of fullerenes to acquire the desired exterior functionality is of major importance to utilize them effectively as bulk materials in practical applications. In last year Read More

Cyanoacetylindoles (CAIs) are easily obtained from the reaction of indoles and cyanoacetic acid, and are used as versatile starting materials in the synthesis of different heterocycles. This review focuses on the application of CAIs to generate a large diversity of indolyl heterocycles such as pyrazoles, triazoles, pyridines, dihydropyridines, pyrimidines, ozathiols, thiophenes, oxazoles, quinolines and many other complex heterocycles.

In this review, the relevance of the combined use of the microwave (MW) and phase transfer catalytic (PTC) techniques is studied within alkylations. In the solid–liquid phase C-alkylation of a series of simple CH-acidic compounds including P=O containing derivatives, in most cases there is no need to use a phase transfer catalyst, as MW promotes the reaction in itself. In the MW-assisted solid–liquid phase alkylation of phenol derivati Read More

The catalytic asymmetric vinylogous-type reactions of γ-butenolides, have received growing attention, because the resulting enantiomerically pure γ-substituted butenolides are versatile building blocks for various natural products and biologically active compounds. The related reactions, such as vinylogous aldol reaction, vinylogous Mannich reaction, vinylogous Michael reactions, as well as allylic alkylation reaction, have been Read More

A synthesis of novel three-, four-, and sixfold branched triazoles 3-5 and triazolothiadiazines 7, 8 and 10, which are linked to a benzene core via sulfanylmethylene spacers was reported. The reaction proceeded via initial treatment of the appropriate poly(bromomethyl)arenes 2 with the corresponding equivalents of 4-amino-4H-1,2,4-triazoles 1 in refluxing ethanolic KOH to give poly(triazolyl)arenes 3-5. Subsequent reacti Read More

Reaction of ethyl propiolate with benzylidenemalononitrile 1a in the presence of L-proline was observed to produce the pyran derivative 7 in 80% yield. In contrast, diethyl acetylenedicarboxylate (6b) does not react with 1a in presence of L-proline. However when DABCO is used as the amine nucleophile, 6b reacts with 1a to form diethyl 5-amino-4,6-dicyano-3-phenyl-2,3-phthalate (20a). The structures of 7 and 20a were assig Read More

We report a convenient access to tertiary carbinamines bearing a gem-diaryl group by Cu-catalyzed aryl Grignard addition to cyclic sulfamidate imines and sulfamide imines. The synthesis of hetero-functionalized 1,2-ethylene derivatives by ring-opening of the resulting sulfamidates is also described.

A highly efficient formal inverse electron demand aza Diels–Alder reaction of 1,2-diaza-1,3-dienes (DDs) is accomplished using dehydroalanine esters (DhAs) as electron-rich dienophiles. Both diastereoisomers of unprecedented α,α-disubstituted cyclic tetrahydropyridazine amino acids were obtained in excellent yields, in refluxing acetonitrile without activation.

Grignard reactions with the Weinreb amide (N-methoxy-N-methylamide) of indole-3-acetic acid provide a facile access to indol- 3-yl ketones, which are potential agonists of the human aryl hydrocarbon receptor ("dioxin receptor"). Addition of one equivalent of the MgBr2•THF complex avoids discolorations and oxidative side reactions, for which the 3-indolyl system is notorious. The product ketones carry aliphatic, olefinic, as w Read More