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Synthesis of spiro[indoline-3,1'-quinolizines] and spiro[indoline-3, 4'-pyrido[1,2-a]quinolines] via three-component reactions of azaarenes, acetylenedicarboxylate, and 3-methyleneoxindoles.

ABSTRACT: The three-component reactions of substituted pyridines, dimethyl acetylenedicarboxylates, and 3-phenacylideneoxindoles afforded spiro[indoline-3,1'quinolizines] in high yields and with high diastereoselectivity. The Diels-Alder reactions of spiro[indoline-3,1' quinolizines] with maleic anhydride and N- phenyl maleimides successfully resulted in polyfunctionalized isoquinolinuclidine derivatives. The similar three-component reactions with quinoline resulted in the novel spiro[indoline-3,4' -pyrido[1,2-a]quinolines] in moderate to good yields.

SUBMITTER: Sun J

PROVIDER: S-EPMC3836201 | biostudies-literature | 2013 Nov

REPOSITORIES: biostudies-literature

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Synthesis of spiro[indoline-3,1'-quinolizines] and spiro[indoline-3, 4'-pyrido[1,2-a]quinolines] via three-component reactions of azaarenes, acetylenedicarboxylate, and 3-methyleneoxindoles.

Sun Jing J Gong Hui H Sun Yan Y Yan Chao-Guo CG

Molecular diversity 20130719 4

The three-component reactions of substituted pyridines, dimethyl acetylenedicarboxylates, and 3-phenacylideneoxindoles afforded spiro[indoline-3,1'quinolizines] in high yields and with high diastereoselectivity. The Diels-Alder reactions of spiro[indoline-3,1' quinolizines] with maleic anhydride and N- phenyl maleimides successfully resulted in polyfunctionalized isoquinolinuclidine derivatives. The similar three-component reactions with quinoline resulted in the novel spiro[indoline-3,4' -pyrid ...[more]

PMID: 23868182

Similar Datasets

Synthesis of functionalized spiro[indoline-3,4'-pyridines] and spiro[indoline-3,4'-pyridinones] via one-pot four-component reactions.

Project description:In the presence of triethylamine as catalyst, the one-pot four-component reactions of arylamines, methyl propiolate, isatin and malononitrile afforded the functionalized spiro[indoline-3,4'-pyridine] derivatives in good yields. Similar reactions with ethyl cyanoacetate successfully afforded the functionalized spiro[indoline-3,4'-pyridines] and spiro[indoline-3,4'-pyridinones] as the main products according to the structures of the arylamines and other primary amines.

| S-EPMC3678513 | biostudies-literature

5,6-Dimeth-oxy-4',5'-diphenyl-indane-2-spiro-3'-pyrrolidine-2'-spiro-3''-indoline-1,2''-dione.

Project description:In the title compound, C(33)H(28)N(2)O(4), the central pyrrolidine ring adopts a half-chair conformation. Both the indolinone and indanone groups are twisted, with their five-membered rings adopting a half-chair and an envelope conformation, respectively. The two benzene rings and the mean plane of the indolinone and indanone groups make dihedral angles of 71.98 (10), 84.32 (10), 86.26 (9) and 78.50 (9)°, respectively, with the central pyrrolidine ring. Intra-molecular C-H⋯O hydrogen bonds stabilize the mol-ecular conformation. In the crystal, pairs of inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers. The dimers are inter-connected into ribbons propagating along [110] via weak inter-molecular C-H⋯O hydrogen bonds. Weak inter-molecular C-H⋯π and π-π [centroid-centroid distance = 3.6509 (11) Å] inter-actions are also observed.

| S-EPMC2983396 | biostudies-literature

3',4'-Dihydro-2'H-spiro[indoline-3,1'-isoquinolin]-2-ones as potential anti-cancer agents: synthesis and preliminary screening.

Project description:Both tetrahydroisoquinolines (THIQs) and oxindoles (OXs) display a broad range of biological activities including anti-cancer activity, and are therefore recognized as two privileged scaffolds in drug discovery. In the present study, 24 3',4'-dihydro-2'H-spiro[indoline-3,1'-isoquinolin]-2-ones, designed as molecular hybrids of THIQ and OX, were synthesized and screened in vitro against 59 cell lines in the NCI-60 screen. Twenty compounds displayed weak to moderate inhibition of cell proliferation; among them, three compounds displayed at least 50% inhibition of cell proliferation. The compounds appeared to target primarily renal cell cancer lines; however, leukaemia, melanoma, non-small cell lung cancer, prostate, ovarian and even breast cancer cell lines were also affected. Therefore, this class of spirooxindoles may provide useful leads in the search for new anti-cancer agents.

| S-EPMC7029914 | biostudies-literature

1''-Benzyl-1'-methyl-4'-(naphthalen-1-yl)naphthalene-2-spiro-3'-pyrrolidine-2'-spiro-3''-indoline-1,2''-dione.

Project description:In the title compound, C(38)H(32)N(2)O(2), the pyrrolidine ring adopts an envelope conformation, whereas the cyclo-hexa-none ring in the tetra-hydro-naphthalene fused-ring system adopts a half-chair conformation. The benzyl ring is oriented at an angle of 67.1?(1)° with respect to the naphthyl ring system. Four intra-molecular C-H?O close contacts and C-H?? inter-action are observed. In the crystal, mol-ecules associate via C-H?O hydrogen bonds, forming a C(12) chain motif along the ac plane.

| S-EPMC3151757 | biostudies-literature

Spiro-[cyclo-pentane-1,2'(1'H)-pyrido[2,3-d]pyrimidin]-4'(3'H)-one.

Project description:The title compound, C(11)H(13)N(2)O, was obtained by cyclo-condensation of 2-amino-pyridine-3-carbonitrile with cyclo-penta-none. The mol-ecule is built up from two fused six-membered rings and one five-membered ring linked through a spiro C atom. Both the pyrimidine and the cyclo-pentane rings adopt envelope conformations. In the crystal structure, mol-ecules are linked by inter-molecular N-H⋯O hydrogen bonds.

| S-EPMC3008029 | biostudies-literature

(1'S)-4-(3,4-Dichlorophenyl)-1'-(3,5-dimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-2-spiro-2'-pyrrolizidine-3'-spiro-3''-indoline-1,2''-dione.

Project description:In the title compound C(37)H(32)Cl(2)N(2)O(4), the unsubstituted pyrrolidine ring shows a twist conformation whereas the substituted pyrrolidine ring shows an envelope conformation. The dimeth-oxy benzene ring is perpendicular to the tetra-lone ring, making a dihedral angle of 89.94?(5)°. Mol-ecules are linked into centrosymmetric dimers by N-H?O hydrogen bonds and the crystal structure is stabilized by C-H?? inter-actions and C-H?O hydrogen bonds. One meth-oxy group is disordered over two positions with the site occupancy factors of 0.84?(2) and 0.16?(2).

| S-EPMC2959408 | biostudies-literature

1',1''-Dimethyl-4'-(naphthalen-1-yl)-1,2,3,4-tetra-hydro-naphthalene-2-spiro-3'-pyrrolidine-2'-spiro-3''-indoline-1,2''-dione.

Project description:In the title compound, C(32)H(28)N(2)O(2), the pyrrolidine ring adopts an envelope conformation, whereas the cyclo-hexa-none ring in the tetra-hydro-naphthalene fused-ring system adopts a half-chair conformation. The oxindole ring system is oriented at an angle of 48.2 (1)° with respect to the naphthyl ring system. An intra-molecular C-H⋯O close contact is observed. In the crystal, mol-ecules associate via two C-H⋯O hydrogen bonds, forming R(2) (2)(14) and R(2) (2)(10) dimers.

| S-EPMC3099991 | biostudies-literature

6'-Bromo-1'H-spiro-[cyclo-hexane-1,2'-pyrido[2,3-d]pyrimidin]-4'(3'H)-one.

Project description:The title compound, C(12)H(14)BrN(3)O, is built up from two fused six-membered rings and one six-membered ring linked through a spiro C atom. The hydro-pyrimidine ring has an envelope conformation and the cyclo-hexane ring is in a chair conformation. In the crystal, mol-ecules are linked by N-H?O and N-H?N hydrogen bonds, forming a mol-ecular tape along the b axis.

| S-EPMC3254517 | biostudies-literature

Methyl (3S,10b'S)-5-chloro-9'-fluoro-1-methyl-2-oxo-5'-phenyl-10b'H-spiro-[indoline-3,1'-pyrazolo-[3,2-a]iso-quinoline]-2'-carboxyl-ate.

Project description:In the title compound, C27H19ClFN3O3, the pyrazole ring has a twist conformation and the six-membered ring to which it is fused has a screw-boat conformation. The mean plane of the pyrazole ring is inclined to the 2-methyl-indoline ring by 85.03 (9) and by 28.17 (8)° to the mean plane of the iso-quinoline ring system. In the crystal, mol-ecules are linked by pairs of C-H⋯F hydrogen bonds, forming inversion dimers. These dimers are linked via C-H⋯O hydrogen bonds, forming a two-dimensional network lying parallel to (10-1).

| S-EPMC3684913 | biostudies-literature

Electron-Transfer-Enabled Concerted Nucleophilic Fluorination of Azaarenes: Selective C-H Fluorination of Quinolines.

Project description:Direct C-H fluorination is an efficient strategy to construct aromatic C-F bonds, but the cleavage of specific C-H bonds in the presence of other functional groups and the high barrier of C-F bond formation make the transformation challenging. Progress for the electrophilic fluorination of arenes has been reported, but a similar transformation for electron-deficient azaarenes has remained elusive due to the high energy of the corresponding Wheland intermediates. Nucleophilic fluorination of electron-deficient azaarenes is difficult owing to the identity of the Meisenheimer intermediate after fluoride attack, from which fluoride elimination to regenerate the substrate is favored over hydride elimination to form the product. Herein, we report a new concept for C-H nucleophilic fluorination without the formation of azaarene Meisenheimer intermediates through a chain process with an asynchronous concerted F--e--H+ transfer. The concerted nucleophilic aromatic substitution strategy allows for the first successful nucleophilic oxidative fluorination of quinolines.

| S-EPMC10515641 | biostudies-literature

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