Synthesis of Various <i>N</i>‐Substituted 4‐Aryloxy/Thiophenoxy/Thioisopropyloxy‐Phthalimides

Kumar, Vipan; Chand, Karam; Chorell, Erik

doi:10.1002/slct.201700721

Cited by 5 publications

(16 citation statements)

References 18 publications

(7 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…5, 146.6 -146.4 (m), 145.1 -144.8 (m), 144.5 -144.1 (m), 142.9 -142.6 (m), 130.7, 129.5, 129.0, 126.6, 113.7 (d, J = 7.5 Hz) ppm. 19 F NMR (235 MHz, CDCl3) δ = -135.08 (q, J = 9.5 Hz, 2F), -141.56 (q, J = 9.5 Hz, 2F) ppm.…”

Section: General Procedures For the Synthesis Of The Fluorinated Phthalimidesmentioning

confidence: 99%

“…The C-F carbons were not detected. 19 F NMR ( 282 276 (65), 249 (10), 202 (6), 176 (17), 148 (100), 116 (9).…”

Section: 456-tetrafluoro-n-(4'-cyanophenyl)phthalimide 3ementioning

confidence: 99%

“…3, 147.3, 146.8 -146.4 (m), 145.0 -144.8 (m), 144.6 -144.3 (m), 142.9 -142.6 (m), 130.9, 125.8, 124.3, 116.5 -111.5 (m), 29.6, 24.1 ppm. 19 F NMR (235 MHz, CDCl3) δ = -134.38 (q, J = 9.6 Hz, 2F), -141.69 (q, J = 9.6 Hz, 2F) ppm. 11), 336 (100), 322 (18), 318 (37), 304 (34), 294 (30), 202 ( 8), 177 ( 13), 160 (15), 148 ( 22), 128 (12), 117 ( 14), 115 ( 19) 103 ( 9), 91 (16).…”

Section: N-(2'6'-mentioning

confidence: 99%

“…3,154.8 (dd,J = 261.6,15.2 Hz),131.5,129.3,128.7 (t,J = 5.6 Hz),128.5,126.5, ppm. 19 F NMR (235 MHz, CDCl3) δ = -124.89 ppm.…”

Section: 5-difluoro-n-phenylphthalimide 3g 6amentioning

confidence: 99%

“…2935,1771,1697,1612,1482,1441,1397,1361,1333,1280,1262,1229,1175,1079,1049,941,915,848,824,776,754,740,708,671,648,607,549,535,516, 438 cm -1 . 8), 178 (100), 166 ( 9), 148 (19), 122 (18), 94 (21).…”

Section: N-butyl-4-fluorophthalimide 3jmentioning

confidence: 99%

See 4 more Smart Citations

Modular Synthesis of Carbazole-Substituted Phthalimides as Potential Photocatalysts

et al. 2021

View full text Add to dashboard Cite

Herein, we report the modular synthesis of carbazole functionalized phthalimides (PI), and demonstrated their applicability as catalyst in selected photocatalytic transformations. The developed synthetic approach provides high variability of phthalimide considering that the synthesis of the phthalimide core can be easily performed. Starting from fluorophthalic acid anhydrides, the corresponding fluorophthalimides were prepared with various amines, and the fluoro function ensured the introduction of carbazoles into the phthalimide framework through aromatic nucleophilic substitution. Besides the synthetic developments, we tested some of the carbazolyl phthalimides in four different photocatalytic transformations, and found attractive and comparable activity to the known 4-CzIPN and noble metal complexes.

show abstract

Section: General Procedures For the Synthesis Of The Fluorinated Phthalimidesmentioning

confidence: 99%

“…The C-F carbons were not detected. 19 F NMR ( 282 276 (65), 249 (10), 202 (6), 176 (17), 148 (100), 116 (9).…”

Section: 456-tetrafluoro-n-(4'-cyanophenyl)phthalimide 3ementioning

confidence: 99%

Section: N-(2'6'-mentioning

confidence: 99%

“…3,154.8 (dd,J = 261.6,15.2 Hz),131.5,129.3,128.7 (t,J = 5.6 Hz),128.5,126.5, ppm. 19 F NMR (235 MHz, CDCl3) δ = -124.89 ppm.…”

Section: 5-difluoro-n-phenylphthalimide 3g 6amentioning

confidence: 99%

Section: N-butyl-4-fluorophthalimide 3jmentioning

confidence: 99%

See 3 more Smart Citations

Modular Synthesis of Carbazole-Substituted Phthalimides as Potential Photocatalysts

et al. 2021

View full text Add to dashboard Cite

show abstract

N‐Heterocyclic Carbene Control over Multiple Stereogenicities: Atroposelective Synthesis of Axially Chiral Phthalimides

et al. 2023

View full text Add to dashboard Cite

The design of a NHC‐catalyzed methodology for the straightforward access to hitherto unknown axially chiral N‐aryl phthalimides has provided a breakthrough in the field of multichirality control. Anticipating a formal (4+2) oxidative annulation, the use of NHC‐derived chiral dienolate as ambident partner toward N‐aryl maleimides unexpectedly yields original bis‐succinimide‐type compounds featuring a multichiral architecture with up to four stereogenic centers and two remote chiral axes. The overall pseudo‐three components reaction between an enal and two equivalents of a N‐aryl maleimide proceeds with excellent enantioselectivity and complete diastereoselectivity. This study illustrates the high synthetic potential of chiral NHC‐activated dienolates for the rapid and highly diastereo‐ and enantioselective preparation of underexplored atropisomers in the pentatomic series, featuring multiple stereogenic elements including challenging Csp2−N chiral axes. The practicality of this reaction is highlighted by a broad substrate scope and a scaled‐up synthesis. Moreover, the easy base‐induced transformation of the chiral bis‐succinimide precursors allows to prepare the initially planned N‐aryl phthalimide atropisomers with excellent retention of enantiopurity.

show abstract

Microwave‐Assisted Highly Efficient Route to 4‐Aminoquinoline‐Phthalimide Conjugates: Synthesis and Anti‐Tubercular Evaluation

et al. 2017

Self Cite

View full text Add to dashboard Cite

Microwave assisted synthesis of 4-aminoquinoline-phthalimides was carried out in order to probe their anti-tubercular potential. Different conditions were screened both under conventional and microwave heating and the best results were obtained by microwave heating in DMSO at 160 o C for 2 min affording the desired 4-aminoquinoline-phthalimides in quantitative yields. Anti-tubercular evaluation against mc 2 6230 strain of Mycobacterium tuberculosis revealed 3 e, having an octyl chain length as spacer, to be the most potent of the synthesized compounds exhibiting MIC 99 of 13.7 mM.

show abstract

Synthesis of Various N‐Substituted 4‐Aryloxy/Thiophenoxy/Thioisopropyloxy‐Phthalimides

Cited by 5 publications

References 18 publications

Modular Synthesis of Carbazole-Substituted Phthalimides as Potential Photocatalysts

Modular Synthesis of Carbazole-Substituted Phthalimides as Potential Photocatalysts

N‐Heterocyclic Carbene Control over Multiple Stereogenicities: Atroposelective Synthesis of Axially Chiral Phthalimides

Microwave‐Assisted Highly Efficient Route to 4‐Aminoquinoline‐Phthalimide Conjugates: Synthesis and Anti‐Tubercular Evaluation

Contact Info

Product

Resources

About