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Mohammad B. Teimouri ; Irena Deperasińska ; Matt Rammo , et al. JOC,2024,89(7):4657-4672. DOI: 10.1021/acs.joc.3c02916
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Abstract: A straightforward route to 1,4-dihydropyrrolo[3,2-b]pyrroles comprised of two electron-withdrawing quinoline or tetrazolo[1,5-a]quinoline scaffolds has been developed. The versatile multicomponent reaction affording 1,4-dihydropyrrolo[3,2-b]pyrroles combined with intramolecular direct arylation enables assembly of these products in just three steps from anilines with overall yields exceeding 30%. The planarized, ladder-type heteroacenes possess up to 14 conjugated rings. These nominally quadrupolar materials exhibit efficient fluorescence with wavelengths spanning most of the visible spectrum from green–yellow for the dyes possessing biaryl bridges and orange–red for the fully fused systems. In many cases, the fluorescence quantum yields are large, the solvatofluorochromic effects are strong, and the fluorescence is maintained even in crystalline state. Analysis of the electronic structure of these molecular architectures using quantum chemical methods suggests that the character and position of the flanking heterocycle determine the shape of HOMO and LUMO and their extension to N-aryl substituents, influencing the values of molar absorption coefficient. An experimental study of the two-photon absorption (2PA) properties has revealed that it occurs in the 700–800 nm range with apparent deviation from the Laporte parity selection rule, which may be attributed to Hertzberg–Teller contribution to vibronically allowed 2PA transition.
Purchased from AmBeed: 612-62-4 ; 73568-25-9 ; 132493-79-9
CAS No. : | 73568-25-9 | MDL No. : | MFCD00130079 |
Formula : | C10H6ClNO | Boiling Point : | - |
Linear Structure Formula : | (H)C9H4NClCHO | InChI Key : | SDKQWXCBSNMYBN-UHFFFAOYSA-N |
M.W : | 191.61 | Pubchem ID : | 690958 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 110℃; for 4.83h; | Example 39; Synthesis of (3,5-bis-trifluoromethyl-benzyl)- [2-(4-cyclohexylmethyI-piperazin-l-yl)- quinolin-3-ylmethyl]-carbamic acid ethyl ester; Step (i): Synthesis of 2-(4-cyclohexylmethyl-piperazin-l-yl)-quinoline-3-carbaldehyde; l-(Cyclohexylmethyl)piperazine (0.42 niL, 2.2 mmol) was added to a mixture of 2-chloro-3-quinolinecarboxaldehyde (0.383 g, 2.0 mmol) and potassium carbonate (0.7 g, 5.0 mmol) in anhydrous DMF (4 mL) at ambient temperature under a nitrogen atmosphere. After being stirred for 20 minutes, the reaction mixture was heated at 110 C for 4.5 h. After cooling to room temperature this mixture was diluted with water (40 mL) and extracted with ethyl acetate (3 x 30 mL). The combined organic extracts were EPO <DP n="205"/>washed with brine, dried over sodium sulfate, filtered, and then concentrated under vacuum to give a pale brown crude product. Purification by silica gel column chromatography and eluting with 2.5% methanol in dichloromethane afforded the title compound (0.56 g), yield: 86%.Mp 95-96 C;1H NMR (CDCl3, 300 MHz): δ 10.17 (s, IH), 8.48 (s, IH), 7.81 (t, J= 8.2 Hz, 2H), 7.67(m, IH), 7.36 (m, IH), 3.51 (t, J= 5.1 Hz, 4H), 2.61 (t, J= 4.8 Hz, 4H), 2.22 (d, J= 7.2Hz, 2H), 1.84-1.68 (m, 6H), 1.31-1.13 (m, 3H), 0.96-0.82 (m, 2H).777/z MS: 338 (M++., 100%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With potassium fluoride; In N,N-dimethyl-formamide; at 120 - 130℃; | General procedure: A mixture of 1a-c (1.93 g, 10 mmol), 4 (1.76 g, 10mmol) and KF (18 mmol) were heated at 120-130 °C inDMF (30 mL) for 16 - 18 h. At the end of this period, thereaction mixture was cooled to room temperature and dilutedwith water (30 mL). The separated solid was filtered, washedand dried to obtain crude 5a-i. The obtained crude productwas then purified by recrystallization using ethanol |
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