Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles

Vaillard, Victoria A.; Budén, María Eugenia; Martín, Sandra Elizabeth; Rossi, Roberto A.

doi:10.1016/j.tetlet.2009.04.042

Cited by 25 publications

(14 citation statements)

References 21 publications

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“…, 99 (12), 125 (47), 127 (17), 140 (55), 154 (9), 182 (6), 202 (100), 237 (7). ESI-HRMS m/z [M + H] + calcd for C 13 H 17 ClNO 238.0999, found 238.1002.…”

Section: ■ Conclusionmentioning

confidence: 99%

“…Isolated (46 mg, 29% yield) by radial thin-layer chromatography eluted with petroleum ether−ethyl ether, 50:50. 1 (25), 91 (4), 107 (5), 115 (5), 123 (6), 150 (11), 152 (14), 165 (40), 166 (23), 183 (18), 184 (3), 199 (18), 201 (11), 208 (6), 213 (22), 228 (9), 241 (14), 271 (11), 288 (20), 289 (17), 291 (100), 292 (28), 305 (15), 306 (45), 330 (1), 346 (97), 347 (24), 348 (21) (13), 117 (10), 128 (13), 129 (22), 130 (100), 131 (49), 132 (16), 144 (7), 158 (6), 172 (10), 173 (36), 174 (6)…”

Section: ■ Conclusionmentioning

confidence: 99%

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Experimental and Computational Study of 6-exo and 7-endo Cyclization of Aryl Radicals Followed by Tandem S_RN1 Substitution

Peisino

Pierini

2013

J. Org. Chem.

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The reaction of N-allyl-N-(2-halobenzyl)-acetamides and derivatives was investigated in liquid ammonia under irradiation with the nucleophiles Me3Sn(-), Ph2P(-) and O2NCH2(-). Following this procedure, novel substituted 2-acetyl-1,2,3,4-tetrahydroisoquinolines and substituted 2-acetyl-2,3,4,5-tetrahydro-1H-benzo[c]azepines were obtained in good yields. These reactions are proposed to occur through the intermediacy of aryl radicals, which by intramolecular 6-exo or 7-endo attack to a double bond cyclize to give aliphatic radicals, which react along the propagation steps of the S(RN)1 chain cycle to afford the cyclic substituted compounds as main products. The reactions were modeled with DFT methods, which provide a rational understanding that relates the product distribution to the structure of the aliphatic radicals proposed as intermediates and the kinetic of their formation.

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“…, 99 (12), 125 (47), 127 (17), 140 (55), 154 (9), 182 (6), 202 (100), 237 (7). ESI-HRMS m/z [M + H] + calcd for C 13 H 17 ClNO 238.0999, found 238.1002.…”

Section: ■ Conclusionmentioning

confidence: 99%

Section: ■ Conclusionmentioning

confidence: 99%

Experimental and Computational Study of 6-exo and 7-endo Cyclization of Aryl Radicals Followed by Tandem S_RN1 Substitution

Peisino

Pierini

2013

J. Org. Chem.

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“…By applying the above methods, a wide range of indolo[2,3- c ]quinolinones can be easily prepared in moderate to high yields. In addition, the indolo[2,3- c ]quinolin-6(7 H )-one framework can also be assembled using other existing strategies including lactamization catalyzed by platinum, combination of acid-catalyzed rearrangements, the Fischer indol synthesis, and the enlargement of the lactam ring, Pd-catalyzed cross-coupling reactions, − and photostimulated S RN 1 reaction . It is worth mentioning, that indolo[2,3- c ]quinolinones are not the target molecules of these publications, only presented as unique examples.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Indolo[2,3-c]quinolin-6(7H)-ones and Antimalarial Isoneocryptolepine. Computational Study on the Pd-Catalyzed Intramolecular C–H Arylation

et al. 2020

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The synthesis of variously substituted indolo[2,3c]quinolin-6(7H)-ones was developed via Pd-catalyzed intramolecular C−H arylation. This method highlights a strategy for preparing indoloquinoline precursors bearing versatile functional groups and provides a new approach for the synthesis of antimalarial isoneocryptolepine analogues. The plausible ring closure mechanism was examined with quantum chemical calculations, where a trigonal bipyramidal concerted metalation− deprotonation transition state is presumable.

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“…The S RN 1 mechanism has clearly manifested to be useful for obtaining heterocyclic compounds . Recently, the S RN 1 reaction was applied to form new C–C bonds in the synthesis of heterocycles such as phenanthridines and benzophenanthridines, phenanthrolines, 1-phenyl-1-oxazolyl-Indane derivatives, cyclopenta-oxazolo-isoquinolin-6-ones carbazoles and carbolines, , pyrrole, indole, and pyrazole fused azaheterocycles . The formation of C-heteroatom bonds is also reported as a consequence of an intramolecular cyclization to generate compounds such as 9 H -carbazoles, among others.…”

Section: Introductionmentioning

confidence: 99%

Photoinduced Synthesis of Dibenzofurans: Intramolecular and Intermolecular Comparative Methodologies

et al. 2018

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The S1 reaction has been used as a powerful tool for the synthesis of heterocycles, and only a few studies about photoinduced intramolecular cyclization to generate a new C-O bond by a radical pathway have been reported. This work introduces two strategies for the synthesis of substituted dibenzofurans by electron transfer (eT) reactions. The first one is a three-step process that comprises bromination of o-arylphenols, Suzuki-Miyaura cross-coupling and photoinduced cyclization in order to obtain the above-mentioned products. The second one is a metal-free procedure and does not require any photocatalyst. Different solvents were tested, and the yields ranged from low to moderate. A comparison was established between both methodologies, showing that the second one is the most suitable for the synthesis of dibenzofurans.

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Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles

Cited by 25 publications

References 21 publications

Experimental and Computational Study of 6-exo and 7-endo Cyclization of Aryl Radicals Followed by Tandem S_RN1 Substitution

Experimental and Computational Study of 6-exo and 7-endo Cyclization of Aryl Radicals Followed by Tandem S_RN1 Substitution

Synthesis of Indolo[2,3-c]quinolin-6(7H)-ones and Antimalarial Isoneocryptolepine. Computational Study on the Pd-Catalyzed Intramolecular C–H Arylation

Photoinduced Synthesis of Dibenzofurans: Intramolecular and Intermolecular Comparative Methodologies

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Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles

Cited by 25 publications

References 21 publications

Experimental and Computational Study of 6-exo and 7-endo Cyclization of Aryl Radicals Followed by Tandem SRN1 Substitution

Experimental and Computational Study of 6-exo and 7-endo Cyclization of Aryl Radicals Followed by Tandem SRN1 Substitution

Synthesis of Indolo[2,3-c]quinolin-6(7H)-ones and Antimalarial Isoneocryptolepine. Computational Study on the Pd-Catalyzed Intramolecular C–H Arylation

Photoinduced Synthesis of Dibenzofurans: Intramolecular and Intermolecular Comparative Methodologies

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Experimental and Computational Study of 6-exo and 7-endo Cyclization of Aryl Radicals Followed by Tandem S_RN1 Substitution

Experimental and Computational Study of 6-exo and 7-endo Cyclization of Aryl Radicals Followed by Tandem S_RN1 Substitution