Phase Transfer Catalyzed Addition of N-Diphenylmethylene-[2-furfuryl]-amine to Schiff Bases

Popandova-Yambolieva, K.

doi:10.1080/00397919008053111

Cited by 6 publications

(1 citation statement)

References 6 publications

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“…A 50-g (515 mmol) sample of furfurylamine, 1 L of toluene, benzophenone (78 g (430 mmol)), and BF 3 ·OEt 2 (5.5 mL (43 mmol)) were placed in a 2-L round-bottom flask with a Dean−Stark trap and heated at reflux for 12 h. The solvent was removed under reduced pressure to give imine 29 as a yellow solid. Recrystallization from MeOH gave 101 g (90%) of pure white crystals: mp 51−53 °C (lit . mp 52−53 °C); IR (thin film) 1623, 1576, 1446, 1290, and 1006 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 4.57 (s, 2H), 6.24 (dd, 1H, J = 3.2 and 0.8 Hz), 6.34 (dd, 1H, J = 3.2 and 2.0 Hz), 7.25 (m, 2H), 7.35 (m, 4H), 7.48 (m, 3H), 7.67 (m, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 51.1, 106.3, 110.2, 127.7, 128.0, 128.6, 130.1, 136.3, 139.5, 141.6, 153.7, and 169.9.…”

Section: Methodsmentioning

confidence: 99%

A Flexible Approach toward Trisubstituted Piperidines and Indolizidines: Synthesis of 6-epi-Indolizidine 223A

Harris

Padwa

2003

J. Org. Chem.

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2,5,6-Trisubstituted piperidines are readily prepared by a combination of an aza-Achmatowicz oxidation of a furyl-substituted benzenesulfonamide followed by a conjugate addition to the resulting 2H-pyridone and subsequent addition of various nucleophiles to a transient N-sulfonyliminium ion. The stereochemistry of the conjugate addition product is the result of axial attack from the face opposite the diaxial substituents at C(2) and C(6). This can be attributed to steric hindrance between the pseudoaxially oriented 2,6-substituents and the equatorially approaching nucleophile, thereby leading to the exclusive formation of the kinetically favored axial 1,4-adduct. Indolizidine alkaloid 223A was isolated from a skin extract of a Panamanian population of the dendrobatid Dendrobates pumilio Schmidt (Dendrobatidae). Synthesis of the originally proposed structure of this alkaloid was achieved in 13 steps in 13.1% overall yield by using an aza-Achmatowicz oxidative rearrangement and a diastereoselective 1,4-conjugate addition as the key steps. The structure of the natural 223A alkaloid (5b) differs from that of the epi-isomer 5a synthesized in this study in the configuration at the 6-position of the indolizidine ring.

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Section: Methodsmentioning

confidence: 99%

A Flexible Approach toward Trisubstituted Piperidines and Indolizidines: Synthesis of 6-epi-Indolizidine 223A

Harris

Padwa

2003

J. Org. Chem.

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Phase Transfer Catalysis

Mąkosza

Fedoryński

2010

Encyclopedia of Catalysis

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Basic concept of phase transfer catalysis (PTC), specific features of this general methodology for executing organic reactions, and mechanism of catalytic action of PT catalysts are presented. Scope and limitations of application of PTC as a general tool of organic synthesis and advantages offered by this methodology are discussed. These discussions are illustrated by numerous examples of successful use of PTC in a variety of reactions of inorganic anions (substitution and addition reactions, β‐eliminations, oxidations, and reductions), heteroanions, and particularly carbanions (reactions with alkylating agents, carbonyl groups, activated carbon‐carbon multiple bonds, electrophilic arenes, heteroatom electrophiles) and carbenes. Possibility of use of PTC for reactions of metalloorganic compounds and complexes and for enantioselective reactions is discussed.

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ChemInform Abstract: Phase‐Transfer Catalyzed Addition of N‐Diphenylmethylene(2‐furfuryl) amine to Schiff Bases.

Popandova-Yambolieva

1991

ChemInform

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Phase Transfer Catalyzed Addition of N-Diphenylmethylene-[2-furfuryl]-amine to Schiff Bases

Cited by 6 publications

References 6 publications

A Flexible Approach toward Trisubstituted Piperidines and Indolizidines: Synthesis of 6-epi-Indolizidine 223A

A Flexible Approach toward Trisubstituted Piperidines and Indolizidines: Synthesis of 6-epi-Indolizidine 223A

Phase Transfer Catalysis

ChemInform Abstract: Phase‐Transfer Catalyzed Addition of N‐Diphenylmethylene(2‐furfuryl) amine to Schiff Bases.

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