Stereospecific approach to α,β-disubstituted nitroalkenes via coupling of α-bromonitroalkenes with boronic acids and terminal acetylenes

Ganesh, Madhu; Namboothiri, Irishi N. N.

doi:10.1016/j.tet.2007.09.012

Cited by 50 publications

(35 citation statements)

References 115 publications

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“…Especially interesting among compounds of this class are those containing a furan ring [2][3][4][5], because furan is the key structure of many medicines, including the antibiotics Furacilin and cefuroxime, antiulcer drug ranitidine, diuretic furosemide, and anticancer drug lapatinib [6], and 5-bromo-2-(2-bromo-2-nitroethenyl)furan 1 (Furvina) is use in the therapy of dermatological infections [7].…”

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confidence: 99%

Furan-containing gem-bromonitroethenes: Synthesis and reaction with morpholine

2015

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The first time the representative of furan-containing gem-bromonitroethenes 5-nitro-2-(2-bromo-2nitro-ethenyl)furan was synthesized by bromination of 5-nitro-2-(2-nitroethenyl)furan followed by dehydrohalogenation of the dibromide. Morpholine adducts of the synthesized β-substituted gembromonitroethene and its analog with a 5-bromo-2-furyl substituent were obtained. The structures of the gembromonitroethenes and aza adducts were characterized by spectral methods (IR, UV, 1 Н, and 13 C-{ 1 H} NMR, including 1 Н-13 С HMQC and HMBC).

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confidence: 99%

Furan-containing gem-bromonitroethenes: Synthesis and reaction with morpholine

2015

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“…We were inspired to explore a cross-coupling strategy (Table 1, Method #2 ) after reading the work of Namboothiri and Ganesh. 38 They prepared 11 by employing a Suzuki-Miyaura cross-coupling reaction between 2-aryl-1-bromo-1-nitroethenes 22 and arylboronic acids. Thus, our synthesis began with β-nitrostyrenes 21 which were prepared by a Henry reaction of the corresponding benzaldehyde 20 with nitromethane.…”

Section: Results and Discussion28mentioning

confidence: 99%

“…38 To a rt stirred solution of β-nitrostyrene 21 (5.0 mmol) in pyridine (6.5 mmol) and cyclohexane (20 mL), neat Br 2 (6.0 mmol) was added dropwise over 5 min. The cloudy yellow reaction was then heated to reflux and allowed to stir for 4-12 h (monitored by TLC).…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of Unsymmetrical 3,4-Diaryl-3-pyrrolin-2-ones Utilizing Pyrrole Weinreb Amides

et al. 2011

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A regiocontrolled synthesis of unsymmetrical 3,4-diaryl-3-pyrrolin-2-ones has been achieved in three steps from 1,2-diaryl-1-nitroethenes with pyrrole-2-carboxamides (pyrrole Weinreb amides) serving as the key linchpin intermediates. Two different methods for the preparation of the requisite nitroalkenes were investigated: (1) modified Henry reaction between arylnitromethanes and arylimines; and (2) Suzuki-Miyaura cross-coupling reaction of 2-aryl-1-bromo-1-nitroethenes with arylboronic acids. Some difficulty was encountered in the preparation of arylnitromethanes, thus leading to the exploration of a cross-coupling strategy that proved more useful. A Barton-Zard pyrrole cyclocondensation reaction between 1,2-diaryl-1-nitroethenes and N-methoxy-N-methyl-2-isocyanoacetamide gave the corresponding pyrrole Weinreb amides, which were then converted into the desired 3-pyrrolin-2-ones in two steps. Overall, this method allowed for the construction of 3,4-diaryl-3-pyrrolin-2-ones with complete regiocontrol of the substituents with respect to the lactam carbonyl. The utility of this synthetic methodology was demonstrated by the preparation of eight unsymmetrical and symmetrical 3,4-diaryl-3-pyrrolin-2-ones including the N-H lactam analog of the selective COX-II inhibitor, rofecoxib.

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“…In 2007, Ganesh and co‐workers reported an exhaustive study of the coupling of α‐bromonitroethylenes with alkyl‐ and arylboronic acids (Suzuki–Miyaura reaction) and with terminal acetylenes (Sonogashira–Hagihara reaction) 61. Suzuki coupling was performed by heating α‐bromonitrostyrene ( 54q ) and diverse arylboronic acids in toluene at reflux in the presence of sodium hydrogen carbonate (3 equiv.)…”

Section: Gem‐halonitroalkenesmentioning

confidence: 99%

Highly Selective Detection of Nerve‐Agent Simulants with BODIPY Dyes

Barba‐Bon

Costero

Gil

et al. 2014

Chemistry A European J

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Two chromo-fluorogenic probes, each based on the boron dipyrromethene core, have been developed for the detection of nerve-agent mimics. These chemosensors display both a color change and a significant enhancement of fluorescence in the presence of diethylcyanophosphonate (DCNP) and diisopropylfluorophosphate (DFP). No interference from other organophosphorus compounds or acids has been observed. Two portable chemosensor kits have been developed and tested to demonstrate its practical application in real-time monitoring.

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Stereospecific approach to α,β-disubstituted nitroalkenes via coupling of α-bromonitroalkenes with boronic acids and terminal acetylenes

Cited by 50 publications

References 115 publications

Furan-containing gem-bromonitroethenes: Synthesis and reaction with morpholine

Furan-containing gem-bromonitroethenes: Synthesis and reaction with morpholine

Synthesis of Unsymmetrical 3,4-Diaryl-3-pyrrolin-2-ones Utilizing Pyrrole Weinreb Amides

Highly Selective Detection of Nerve‐Agent Simulants with BODIPY Dyes

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