2.3.1. IMDA Reactions of Acetylenic Sulfones 4512 2.3.2. IMDA Reactions of Allenic Sulfones 4513 2.3.3. IMDA Reactions of Dienyl Sulfones 4513 3. 1,3-Dipolar Cycloadditions 4514 3.1. With Azides 4514 3.2. With Diazo Compounds 4515 3.3. With Nitrones 4516 3.4. With Nitrile Oxides 4519 3.5. With Mesoionic Compounds 4519 3.6. With Other 1,3-Dipoles 4519 4. [2 + 2] Cycloadditions 4520 4.1. With Alkenes and Dienes 4520 4.2. Intramolecular [2 + 2] Cycloadditions 4522 4.3. With Imines, Enamines, Ynamines, And Enol Ethers 4522 4.4. Other [2 + 2] Cycloadditions 4523 5. Miscellaneous Cycloadditions 4524 6. Ene Reactions 4524 7. Cyclizations of Bis(allenic) Sulfones and Their Congeners 4526

Cycloadditions and cyclizations of acetylenic, allenic, and conjugated dienyl sulfones.

Palladium-mediated synthesis of poly-fused heterocycles from Baylis–Hillman adducts

A new approach to construction of isoindolo[1,2-a]isoquinoline alkaloids Nuevamine, Jamtine, and Hirsutine via IMDAF reaction

Sequential Insertion of Alkynes and CO or Isocyanides into the Pd–C Bond of Cyclopalladated Phenylacetamides. Synthesis of Eight-Membered Palladacycles, Benzo[d]azocine-2,4(1H,3H)-diones, and Highly Functionalized Acrylonitrile and Acrylamide Derivatives

The multicomponent reaction of l-proline, isatins, and excess of methyl propiolates in methanol unexpectedly afforded 2-(oxoindolin-3-ylidene)propylidene)pyrrolidin-1-yl)acrylates in good yields, and the products subsequently converted to unique nine-membered pyrrolo[1′,2′:1,9]azonino[6,5,4-cd]indoles in the presence of p-TsOH. Furthermore, the multicomponent reaction of l-proline, N-benzylisatins, and excess alkyl propiolates in refluxing chloroform unprecedentedly resulted in eight-membered azocino[1,2-a]benzo[c][1,5]diazocines as the main product. The molecular structures of the polyheterocyclic compounds were confirmed by determination of 19 single crystal structures. The reaction mechanism was believed to contain the sequential 1,3-dipolar cycloaddition, addition of cyclic tertiary amine to excess of propiolate, and fascinating ring opening as well as rearrangement process. The N-substituent on isatins played a critical role in the different reaction patterns.

Construction of Unique Eight- or Nine-Membered Polyheterocyclic Systems via Multicomponent Reaction of l-Proline, Alkyl Propiolate, and Isatin

Synthesis of Benzoazocines from Substituted Tetrahydroisoquinolines and Activated Alkynes in a Tetrahydropyridine Ring Expansion

Tetrahydroisoquinolines underwent tandem piperidine ring enlargement in the presence of activated alkynes in acetonitrile or methanol, producing tetrahydrobenzo[d]azocines in high yields. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

Grigoriy G. Alexandrov

Papers

Synthesis of Benzoazocines from Substituted Tetrahydroisoquinolines and Activated Alkynes in a Tetrahydropyridine Ring Expansion

Synthesis of Benzoazocines from Substituted Tetrahydroisoquinolines and Activated Alkynes in a Tetrahydropyridine Ring Expansion.