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Kannupal Srinivasan - One of the best experts on this subject based on the ideXlab platform.
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Synthesis of 2,3-disubstituted thiophenes from 2-aryl-3-nitro-cyclopropane-1,1-dicarboxylates and 1,4-dithiane-2,5-diol
RSC Advances, 2015Co-Authors: Thangavel Selvi, Govindhraj Vanmathi, Kannupal SrinivasanAbstract:A two-step synthesis of 2,3-disubstituted thiophenes from trans-2-aryl-3-nitrocyclopropane-1,1-dicarboxylates and 1,4-dithiane-2,5-diol is described. The nitrocyclopropane dicarboxylates when treated with boron trifluoride etherate formed aroylmethylidene malonates in situ through ring-opening followed by rearrangement and a Nef Reaction, and subsequent addition of 1,4-dithiane-2,5-diol and triethylamine to the same flask gave tetrahydrothiophenes via a tandem thia-Michael addition/aldol Reaction in a sequential one-pot manner. The product tetrahydrothiophenes upon treatment with p-toluenesulphonic acid underwent dehydration followed by monodecarbethoxylation to afford 2,3-disubstituted thiophenes.
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Boron Trifluoride Mediated Ring-Opening Reactions of trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates. Synthesis of Aroylmethylidene Malonates as Potential Building Blocks for Heterocycles
The Journal of organic chemistry, 2014Co-Authors: Thangavel Selvi, Kannupal SrinivasanAbstract:trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates, upon treatment with BF3·OEt2, undergo ring-opening rearrangement and the Nef Reaction to give aroylmethylidene malonates. The products are found to be potential precursors for heterocycles, such as imidazoles, quinoxalines, and benzo[1,4]thiazines.
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Boron Trifluoride Mediated Ring-Opening Reactions of trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates. Synthesis of Aroylmethylidene Malonates as Potential Building Blocks for Heterocycles
2014Co-Authors: Thangavel Selvi, Kannupal SrinivasanAbstract:trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates, upon treatment with BF3·OEt2, undergo ring-opening rearrangement and the Nef Reaction to give aroylmethylidene malonates. The products are found to be potential precursors for heterocycles, such as imidazoles, quinoxalines, and benzo[1,4]thiazines
Santosh G. Tilve - One of the best experts on this subject based on the ideXlab platform.
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Henry–Nef Reaction: a practical and versatile chiral pool route to 2-substituted pyrrolidine and piperidine alkaloids
Tetrahedron, 2013Co-Authors: Chinmay Bhat, Santosh G. TilveAbstract:The paper describes the synergistic protocol developed by combinatorial Henry and Nef Reaction for the synthesis of 2-substituted pyrrolidine and piperidine alkaloids containing 1,3-aminoketone and 1,3-amino alcohol units. The utility of the protocol is demonstrated by asymmetric synthesis of 12 natural products of which asymmetric synthesis of (−)-N-methylpelletierine is presented for the first time. The one-carbon homologation described also provides an alternate route for the synthesis of key intermediates homoprolinol and homopipecolinol used as synthetic precursors for several alkaloids and construction of β-amino acids from α-amino acids.
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henry Nef Reaction a practical and versatile chiral pool route to 2 substituted pyrrolidine and piperidine alkaloids
Tetrahedron, 2013Co-Authors: Chinmay Bhat, Santosh G. TilveAbstract:The paper describes the synergistic protocol developed by combinatorial Henry and Nef Reaction for the synthesis of 2-substituted pyrrolidine and piperidine alkaloids containing 1,3-aminoketone and 1,3-amino alcohol units. The utility of the protocol is demonstrated by asymmetric synthesis of 12 natural products of which asymmetric synthesis of (−)-N-methylpelletierine is presented for the first time. The one-carbon homologation described also provides an alternate route for the synthesis of key intermediates homoprolinol and homopipecolinol used as synthetic precursors for several alkaloids and construction of β-amino acids from α-amino acids.
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synthesis of hygrine norhygrine pseudohygroline and hygroline via Nef Reaction
Tetrahedron Letters, 2011Co-Authors: Chinmay Bhat, Santosh G. TilveAbstract:Abstract Synthesis of tropane alkaloids (−)-hygrine, (−)-norhygrine and sedum alkaloids (−)-pseudohygroline and (−)-hygroline is described from l -proline via Henry and Nef Reactions.
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Synthesis of (−)-hygrine, (−)-norhygrine, (−)-pseudohygroline and (−)-hygroline via Nef Reaction
Tetrahedron Letters, 2011Co-Authors: Chinmay Bhat, Santosh G. TilveAbstract:Abstract Synthesis of tropane alkaloids (−)-hygrine, (−)-norhygrine and sedum alkaloids (−)-pseudohygroline and (−)-hygroline is described from l -proline via Henry and Nef Reactions.
Laurent El Kaim - One of the best experts on this subject based on the ideXlab platform.
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The Nef Reaction of Isocyanides
Synthesis, 2014Co-Authors: Fabio La Spisa, Gian Cesare Tron, Laurent El KaimAbstract:The interaction of isocyanides with acyl chlorides was first reported by Nef in 1892. The resulting α-keto imidoyl chlorides may be hydrolyzed to form α-keto amides. Relatively few data are available on this Reaction and the chemistry of α-keto imidoyl chlorides has been largely underestimated until some recent uses in intra- and intermolecular couplings with a variety of nucleophiles. The present review brings a comprehensive presentation of the Nef Reaction of isocyanides focusing on mechanism and regioselectivity issues. 1 Isocyanide Chemistry 2 Isocyanide Interaction with Acyl Chlorides and Analogues 2.1 General Considerations 2.2 Methods of Preparation of α-Keto Imidoyl Chlorides 2.3 Nef Reaction Mechanism 3 Reactivity of α-Keto Imidoyl Chlorides 3.1 General Behavior of α-Keto Imidoyl Chlorides 3.2 Intramolecular Trappings 3.3 Intermolecular Trappings and Three-Component Reactions 4 Extensions of the Nef Reaction 5 Conclusion
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The Nef Reaction of Isocyanides
Synthesis, 2014Co-Authors: Gian Cesare Tron, Laurent El Kaim, Fabio La SpisaAbstract:International audienceThe interaction of isocyanides with acyl chlorides was first reported by Nef in 1892. The resulting α-keto imidoyl chlorides may be hydrolyzed to form α-keto amides. Relatively few data are available on this Reaction and the chemistry of α-keto imidoyl chlorides has been largely underestimated until some recent uses in intra- and intermolecular couplings with a variety of nucleophiles. The present review brings a comprehensive presentation of the Nef Reaction of isocyanides focusing on mechanism and regioselectivity issues
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The Nef Reaction of Isocyanides
SYNTHESIS, 2014Co-Authors: Fabio La Spisa, Gian Cesare Tron, Laurent El KaimAbstract:The interaction of isocyanides with acyl chlorides was first reported by Nef in 1892. The resulting α-keto imidoyl chlorides may be hydrolyzed to form α-keto amides. Relatively few data are available on this Reaction and the chemistry of α-keto imidoyl chlorides has been largely underestimated until some recent uses in intra- and intermolecular couplings with a variety of nucleophiles. The present review brings a comprehensive presentation of the Nef Reaction of isocyanides focusing on mechanism and regioselectivity issues.
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A density functional theory study of the Nef-isocyanide Reaction: mechanism, influence of parameters and scope.
The journal of physical chemistry. A, 2011Co-Authors: Nicolas Chéron, Laurent El Kaim, Laurence Grimaud, Paul Fleurat-lessardAbstract:The Nef Reaction between isocyanides and acyl chlorides is studied at the M06-2X/6-311+G(d,p) level of theory in toluene. After proving that the Reaction follows a concerted mechanism instead of an addition-elimination path, we study the influences of the solvent, the isocyanide, the acyl moiety and the leaving group on the energy profile of the Reaction. i The calculated data can be rationalized with the pK a of the leaving group, or more generally with the population of the oxygen lone pairs of the acyl moiety.
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Three-Component Nef-Huisgen Access to 1,2,4-Triazoles
Synlett, 2009Co-Authors: Laurent El Kaim, Laurence Grimaud, Simon WagschalAbstract:We present herein a new three-component triazole synthesis involving a Nef-Huisgen cascade. After the α-addition of acyl chlorides onto isocyanides (Nef Reaction), the resulting-imidoyl chloride is treated with tetrazoles under suitable activation (ZnCl 2 ). The resulting adduct is unstable and evolves according to the Huisgen Reaction.
Thangavel Selvi - One of the best experts on this subject based on the ideXlab platform.
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Synthesis of 2,3-disubstituted thiophenes from 2-aryl-3-nitro-cyclopropane-1,1-dicarboxylates and 1,4-dithiane-2,5-diol
RSC Advances, 2015Co-Authors: Thangavel Selvi, Govindhraj Vanmathi, Kannupal SrinivasanAbstract:A two-step synthesis of 2,3-disubstituted thiophenes from trans-2-aryl-3-nitrocyclopropane-1,1-dicarboxylates and 1,4-dithiane-2,5-diol is described. The nitrocyclopropane dicarboxylates when treated with boron trifluoride etherate formed aroylmethylidene malonates in situ through ring-opening followed by rearrangement and a Nef Reaction, and subsequent addition of 1,4-dithiane-2,5-diol and triethylamine to the same flask gave tetrahydrothiophenes via a tandem thia-Michael addition/aldol Reaction in a sequential one-pot manner. The product tetrahydrothiophenes upon treatment with p-toluenesulphonic acid underwent dehydration followed by monodecarbethoxylation to afford 2,3-disubstituted thiophenes.
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Boron Trifluoride Mediated Ring-Opening Reactions of trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates. Synthesis of Aroylmethylidene Malonates as Potential Building Blocks for Heterocycles
The Journal of organic chemistry, 2014Co-Authors: Thangavel Selvi, Kannupal SrinivasanAbstract:trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates, upon treatment with BF3·OEt2, undergo ring-opening rearrangement and the Nef Reaction to give aroylmethylidene malonates. The products are found to be potential precursors for heterocycles, such as imidazoles, quinoxalines, and benzo[1,4]thiazines.
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Boron Trifluoride Mediated Ring-Opening Reactions of trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates. Synthesis of Aroylmethylidene Malonates as Potential Building Blocks for Heterocycles
2014Co-Authors: Thangavel Selvi, Kannupal SrinivasanAbstract:trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates, upon treatment with BF3·OEt2, undergo ring-opening rearrangement and the Nef Reaction to give aroylmethylidene malonates. The products are found to be potential precursors for heterocycles, such as imidazoles, quinoxalines, and benzo[1,4]thiazines
Chinmay Bhat - One of the best experts on this subject based on the ideXlab platform.
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Henry–Nef Reaction: a practical and versatile chiral pool route to 2-substituted pyrrolidine and piperidine alkaloids
Tetrahedron, 2013Co-Authors: Chinmay Bhat, Santosh G. TilveAbstract:The paper describes the synergistic protocol developed by combinatorial Henry and Nef Reaction for the synthesis of 2-substituted pyrrolidine and piperidine alkaloids containing 1,3-aminoketone and 1,3-amino alcohol units. The utility of the protocol is demonstrated by asymmetric synthesis of 12 natural products of which asymmetric synthesis of (−)-N-methylpelletierine is presented for the first time. The one-carbon homologation described also provides an alternate route for the synthesis of key intermediates homoprolinol and homopipecolinol used as synthetic precursors for several alkaloids and construction of β-amino acids from α-amino acids.
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henry Nef Reaction a practical and versatile chiral pool route to 2 substituted pyrrolidine and piperidine alkaloids
Tetrahedron, 2013Co-Authors: Chinmay Bhat, Santosh G. TilveAbstract:The paper describes the synergistic protocol developed by combinatorial Henry and Nef Reaction for the synthesis of 2-substituted pyrrolidine and piperidine alkaloids containing 1,3-aminoketone and 1,3-amino alcohol units. The utility of the protocol is demonstrated by asymmetric synthesis of 12 natural products of which asymmetric synthesis of (−)-N-methylpelletierine is presented for the first time. The one-carbon homologation described also provides an alternate route for the synthesis of key intermediates homoprolinol and homopipecolinol used as synthetic precursors for several alkaloids and construction of β-amino acids from α-amino acids.
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synthesis of hygrine norhygrine pseudohygroline and hygroline via Nef Reaction
Tetrahedron Letters, 2011Co-Authors: Chinmay Bhat, Santosh G. TilveAbstract:Abstract Synthesis of tropane alkaloids (−)-hygrine, (−)-norhygrine and sedum alkaloids (−)-pseudohygroline and (−)-hygroline is described from l -proline via Henry and Nef Reactions.
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Synthesis of (−)-hygrine, (−)-norhygrine, (−)-pseudohygroline and (−)-hygroline via Nef Reaction
Tetrahedron Letters, 2011Co-Authors: Chinmay Bhat, Santosh G. TilveAbstract:Abstract Synthesis of tropane alkaloids (−)-hygrine, (−)-norhygrine and sedum alkaloids (−)-pseudohygroline and (−)-hygroline is described from l -proline via Henry and Nef Reactions.
