Intramolecular rhodium-catalyzed activation of α-amino C–H bonds: decisive influence of conformational factors in the synthesis of bicyclic aminals from N-sulfamoyloxyacetyl azacycloalkanes

Morin, Marie S. T.; Toumieux, Sylvestre; Compain, Philippe; Peyrat, Sandrine; Kalinowska‐Tłuścik, Justyna

doi:10.1016/j.tetlet.2007.09.148

Cited by 21 publications

(11 citation statements)

References 30 publications

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“…Intramolecular C-HÁ Á ÁO short contacts similar to that observed in the title compounds were found in five compounds in the CSD: LISLAB, 1-(1-pyrrolidinylcarbonyl)cyclopropyl sulfamate (Morin et al, 2007), PEQHAU, 2-[30-(400-chlorophenyl)-40,60-dimethoxyindol-70-yl]glyoxyl-1-pyrrolidine (Black et al, 1997), QIBBEJ, [2-hydroxy-5-(2-hydroxybenzoyl)phenyl](pyrrolidin-1-yl)-methanone (Holtz et al, 2007), SINHAZ, 2-methoxy-1-(1-pyrrolidinylcarbonyl)naphthalene (Sakamoto et al, 2007) and TAJDIR, (4S,5S)-4,5-bispyrrolidinylcarbonyl)-2,2-dimethyl-1,3-dioxolane (Garcia et al, 1991…”

Section: Database Surveysupporting

confidence: 54%

The crystal structures of two new coumarin derivatives: 2-(4-{2-[(2-oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide and N-(2,4-dimethoxybenzyl)-2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide

Abuthahir¹,

NizamMohideen²,

Viswanathan

et al. 2019

Acta Cryst E

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The title compounds, 2-(4-{2-[(2-oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide, C17H19N3O5, (I), and N-(2,4-dimethoxybenzyl)-2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide, C20H19NO6, (II), are new coumarin derivatives. In compound (I), the six-membered piperazine adopts a chair conformation. The dihedral angles between the mean planes of the chromene ring and amide plane is 82.65 (7)° in (I) and 26.2 (4)° in (II). The dihedral angles between the mean planes of the chromene ring and the four planar C atoms of the piperazine ring in (I) and the benzene ring in (II) are 87.66 (6) and 65.0 (4)°, respectively. There are short intramolecular contacts in both molecules forming S(5) ring motifs, viz. N—H...N and C—H...O in (I), and N—H...O and C—H...N in (II). In the crystals of both compounds, molecules are linked by N—H...O hydrogen bonds, forming chains along [1\overline{1}0] in (I) and [010] in (II). The chains are linked by C—H...O hydrogen bonds, forming layers parallel to the ab plane in the crystals of both compounds. In the crystal of (I), there are also C—H...π and offset π–π interactions [intercentroid distance = 3.691 (1) Å] present within the layers. In the crystal of (II), there are only weak offset π–π interactions [intercentroid distance = 3.981 (6) Å] present within the layers. The intermolecular contacts in the crystals of both compounds have been analysed using Hirshfeld surface analysis and two-dimensional fingerprint plots.

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Section: Database Surveysupporting

confidence: 54%

The crystal structures of two new coumarin derivatives: 2-(4-{2-[(2-oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide and N-(2,4-dimethoxybenzyl)-2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide

Abuthahir¹,

NizamMohideen²,

Viswanathan

et al. 2019

Acta Cryst E

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“…Since the nitrogen atoms in substrates 584 a-d, 589, 592, 596 could coordinate to the catalyst through their nitrogen lone pairs, studies were further pursued with N-sulfamoylacetylazacycloalkanes 597 a-f, which possess an amide functionality, thus avoiding undesired coordination. [126] Furthermore, the a-substituents R 1 and R 2 were used to potentially assist the amination reaction by way of the Thorpe-Ingold effect. Disappointingly, when tested under the previously reported conditions for intramolecular amination, piperidine 597 a gave the expected aminal 598 a in only 20 % yield (Scheme 129).…”

Section: Transition-metal-catalyzed C à H Activationmentioning

confidence: 99%

Direct α‐Functionalization of Saturated Cyclic Amines

Mitchell

Peschiulli

Lefèvre

et al. 2012

Chemistry A European J

429

166

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“…Intramolecular C-HÁ Á ÁO short contacts similar to that in (3) are found in five compounds in the CSD: LISLAB, 1-(1pyrrolidinylcarbonyl)cyclopropyl sulfamate (Morin et al, 2007), PEQHAU, 2-[3 0 -(4 00 -chlorophenyl)-4 0 ,6 0 -dimethoxyindol-7 0 -yl]glyoxyl-1-pyrrolidine (Black et al, 1997), QIBBEJ, [2-hydroxy-5-(2-hydroxybenzoyl)phenyl](pyrrolidin-1-yl)methanone (Holtz et al, 2007), SINHAZ, 2-methoxy-1-(1pyrrolidinylcarbonyl)naphthalene (Sakamoto et al, 2007) and TAJDIR, (4S,5S)-4,5-bis(pyrrolidinylcarbonyl)-2,2-dimethyl-1,3-dioxolane (Garcia et al, 1991), Fig. 10.…”

Section: Database Surveymentioning

confidence: 71%

A comparison of the structures of some 2- and 3-substituted chromone derivatives: a structural study on the importance of the secondary carboxamide backbone for the inhibitory activity of MAO-B

et al. 2015

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Intramolecular rhodium-catalyzed activation of α-amino C–H bonds: decisive influence of conformational factors in the synthesis of bicyclic aminals from N-sulfamoyloxyacetyl azacycloalkanes

Cited by 21 publications

References 30 publications

The crystal structures of two new coumarin derivatives: 2-(4-{2-[(2-oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide and N-(2,4-dimethoxybenzyl)-2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide

The crystal structures of two new coumarin derivatives: 2-(4-{2-[(2-oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide and N-(2,4-dimethoxybenzyl)-2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide

Direct α‐Functionalization of Saturated Cyclic Amines

A comparison of the structures of some 2- and 3-substituted chromone derivatives: a structural study on the importance of the secondary carboxamide backbone for the inhibitory activity of MAO-B

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