Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione

• Yan Sun,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2013, 9, 8–14, doi:10.3762/bjoc.9.2

• three-component reaction of arylamine, isatin and cyclopentane-1,3-dione. Results and Discussion Recently we found that the four-component reactions of arylamine, acetylenedicarboxylate, isatin and dimedone in acetic acid resulted in the novel functionalized tetrahydrospiro[indoline-3,2’-quinoline

Organocatalytic C–H activation reactions

• Subhas Chandra Pan

Beilstein J. Org. Chem. 2012, 8, 1374–1384, doi:10.3762/bjoc.8.159

• as the substrate, and the N-alkyl-indoline product 10 was obtained in good yields (70–82%) mainly by the method of the Pan group (Scheme 7). In this case, another molecule of indoline acts as the hydride donor and is converted to indole. Both Tunge and Pan suggested redox isomerization in the

• azomethine ylide intermediates in the Tunge pyrrole formation and in the formation of N-alkylindoles from indoline [19]. These reactions are considered C–H activation reactions, as during the azomethine ylide formation, the C–H bond that is cleaved is not activated by electron-withdrawing (such as ester

Recent developments in gold-catalyzed cycloaddition reactions

• Fernando López and
• José L. Mascareñas

Beilstein J. Org. Chem. 2011, 7, 1075–1094, doi:10.3762/bjoc.7.124

• , when PtCl2 (under an atmosphere of CO) is used, the major products are 2,3-indoline-fused cyclopentenes 44, which arise from a formal (3 + 2) cycloaddition (lower arrow) [86]. Thus, the appropriate choice of a Pt or Au catalyst determines whether the allenyl intermediate 42 participates as a 2C- or as

Mitomycins syntheses: a recent update

• Jean-Christophe Andrez

Beilstein J. Org. Chem. 2009, 5, No. 33, doi:10.3762/bjoc.5.33

• the p-quinone are called mitosanes or mitosenes depending whether they are at the oxidation state of an indoline (Y1 or Y2 = H) or an indole (Y1 = Y2 = C=C). Compounds bearing an aziridine at C1 and C2 are described specifically as aziridinomitosanes and aziridinomitosenes respectively. Compounds

• reagent, N-phenylselenophthalimide (N-PSP) [83][84]. The attack of this reagent upon the double bond led to indoline 81 which underwent a second alkylation to generate the complete pyrroloindole system 82. It is noteworthy that the cyclization reaction was completely stereospecific. Indeed, one could

• argue that the addition of N-PSP to the olefin 80 to form a selenonium ion is reversible and that the attack of the nitrogen is favored when the two large groups emerge trans relative to the indoline ring. Treatment with m-CPBA then created the double bond which was later fashioned into aziridine 84

Reduction of arenediazonium salts by tetrakis(dimethylamino)ethylene (TDAE): Efficient formation of products derived from aryl radicals

• Mohan Mahesh,
• John A. Murphy,
• Franck LeStrat and
• Hans Peter Wessel

Beilstein J. Org. Chem. 2009, 5, No. 1, doi:10.3762/bjoc.5.1

• : cyclization; electron transfer; indole; indoline; radical; Introduction Arenediazonium salts have long proved useful as sources of aryl radicals in many reactions featuring carbon-carbon (e.g., Meerwein [1], Pschorr [2][3], Gomberg [3] reactions) and carbon-heteroatom bond (e.g., Sandmeyer [4]) formation

• vinblastine (58a) and vincristine (58b) contain such a system. Aryl C-C bond formation As a final extension of this methodology, we probed the feasibility of this methodology in aryl-aryl C-C bond formation reactions. Accordingly, the diazonium salt 62 was prepared from indoline (59), and treated with one

• translocation) by the aryl radical 67 from the carbon atom in the α-position to the nitrogen atom of the indoline nucleus within the same molecule. The indolinyl radical 71 might follow pathway A and undergo radical fragmentation to the intermediate 75 which would eventually tautomerise to indole (63). The