Cycloadditions and Cyclizations of Acetylenic, Allenic, and Conjugated Dienyl Sulfones

Abstract

Introduction 4499 2. Diels-Alder Cycloadditions 4499 2.1. Unsaturated Sulfones as Dienophiles 4499 2.1.1. Early Studies 4499 2.1.2. Aromatization of Cycloaddition Products of Acetylenic Sulfones 4501 2.1.3. Iterative Diels-Alder and Ramberg-Backlund Reactions of Chloroalkylsulfonyl Allenes 4502 2.1.4. Diels-Alder Cycloadditions of Bis(sulfonyl)acetylenes and Their Equivalents 4502 2.1.5. Diels-Alder Cycloadditions of Acetylenic Sulfones Containing Heteroatom Substituents 4503 2.1.6. Diels-Alder Reactions of Dienyl Sulfones as Dienophiles 4504 2.1.7. Diels-Alder Reactions of Unsaturated Sulfones with Pyrroles 4505 2.1.8. Diels-Alder Reactions of Unsaturated Sulfones with Furans and Isobenzofurans 4507 2.1.9. Miscellaneous Cycloadditions 4508 2.2. Dienyl Sulfones As the Diene Components in Diels-Alder Reactions 4509 2.2.1. 1-Sulfonyl Derivatives † Dedicated to Professor David N. Harpp, for his inspiring contributions as a teacher, mentor and scholar.

Tosvinyl and Besvinyl as Protecting Groups of Imides, Azinones, Nucleosides, Sultams, and Lactams. Catalytic Conjugate Additions to Tosylacetylene

“…Consequently, they have many synthetic applications. 1 We were interested in the conjugate additions of nucleophiles to ethynyl sulfones, in comparison with those to other electron-deficient triple bonds. 2 In this regard, we planned to take advantage of the reactivity of commercially available 1- (ethynylsulfonyl)-4-methylbenzene (ethynyl p-tolyl sulfone, Ts-C≡CH), commonly called tosylacetylene, to develop a procedure for the protection of heterocyclic compounds with activated NH groups.…”

Synthesis and Biological Evaluation of S-Substituted Perhalo-2-nitrobuta-1,3-dienes as Novel Xanthine Oxidase, Tyrosinase, Elastase, and Neuraminidase Inhibitors

“…Nitro and sulfoxide compounds have many biological activities such as antiulcer, antibacterial, antifungal, anticancer, and antihypertensive activities [10][11][12][13][14][15][16][27][28][29]. However, antixanthine oxidase, antityrosinase, antielastase, and antineuraminidase activities of these compounds have not been investigated until now.…”

“…In the literature, these compounds have been termed as "chemical chameleons." They are used as synthetic mediators in the syntheses of several organic compounds having antiulcer, antibacterial, antifungal, and antihypertensive properties [27][28][29].…”

Regio- and stereoselective Diels-Alder reaction of diphenyl 5-methylhexa-1,3,4-trien-3-yl phosphine oxide with N-(4-substituted-phenyl)maleimides and maleic anhydride

“…An impressive number of carbo-and heterocyclic systems has been prepared from allenic starting materials. [1][2][3][4][5][6] Due to the fact that it allows the selective formation of two carbon-carbon bonds and up to four centers of chirality in a single step, the Diels-Alder reaction is perhaps one of the most important transformations in organic chemistry and is probably the most valuable and most applied reaction in synthetic organic chemistry. [7][8][9][10][11] Among the many different dienes and dienophiles employed in Diels-Alder reaction, allenes have played only a minor role.…”