Photochemistry of .beta.-iodoacrylamides

Wilson, R. Marshall; Commons, Thomas J.

doi:10.1021/jo00908a009

Cited by 12 publications

(2 citation statements)

References 8 publications

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“…First Synthesis of Enynoylindole 40. We envisioned a straightforward synthesis of the cyclization precursor 40 via an acylation of acetyltryptamine ( 37 ) with cis -3-iodoacryloyl chloride, followed by Pd-mediated coupling with trimethylsilylacetylene and desilylation. Surprisingly, conditions that had previously worked well for the acylation of the indole nitrogen failed to yield any of the desired unsaturated amide product.…”

Section: The Ab → Abcd → Abcde → Abcdef Approach To 1: Successful St...mentioning

confidence: 99%

Approaches to the Synthesis of (±)-Strychnine via the Cobalt-Mediated [2 + 2 + 2] Cycloaddition: Rapid Assembly of a Classic Framework

et al. 2001

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Five synthetic approaches to racemic strychnine (1), with the cobalt-mediated [2 + 2 + 2] cycloaddition of alkynes to indoles as the key step, are described. These include the generation and attempted cyclization of macrocycle 8 and the synthesis of dihydrocarbazoles 15, 22, and 26 and their elaboration to pentacyclic structures via a conjugate addition, dipolar cycloaddition, and propellane-to-spirofused skeletal rearrangement, respectively. Finally, the successful total synthesis of 1 is discussed. The development of a short, highly convergent route (14 steps in the longest linear sequence) is highlighted by the cyclization of enynoylindole 40 with acetylene and the formal intramolecular 1,8-conjugate addition of amine 49 to form pentacycle 50. Numerous attempts toward the formation of the piperidine ring of 1 from vinyl iodide 56 were made and its successful formation via palladium-, nickel-, and radical-mediated processes is described.

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Section: The Ab → Abcd → Abcde → Abcdef Approach To 1: Successful St...mentioning

confidence: 99%

Approaches to the Synthesis of (±)-Strychnine via the Cobalt-Mediated [2 + 2 + 2] Cycloaddition: Rapid Assembly of a Classic Framework

et al. 2001

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“…234,235 2,6-Dimethyl-3,4,5,6-tetrahydropyridine was N-acylated with acryloyl chloride in the presence of triethylamine at room temperature. 236 Compound 311 was synthesised in 76% yield by the reaction of the imine 1a with chloride 310 in the presence of Et 3 N in DMF. 237 The thioimidate 7 reacts with acetyl or benzoyl chloride at room temperature to give N-acylated derivatives 312.…”

Section: N-acylation Reactionsmentioning

confidence: 99%

2,3,4,5-Tetrahydropyridine (Δ¹-piperideine) and its derivatives. Synthesis and chemical properties

Shvekhgeimer¹

1998

Russ. Chem. Rev.

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We study the influence of the tetragonalization occurring during the martensitic phase transition on the exchange interactions in Ni 2 MnGa Heusler alloy using first-principles calculations in conjunction with the frozen-magnon approximation. We show that the tetragonalization alters only the exchange constants characterizing the Mn-Mn interactions. Calculated Curie temperatures within the random-phase approximation are found to agree with experimental data. Moreover, we study the temperature dependence of the magnetization and the small deviation from the experimental data exactly at the temperature of the phase transition is discussed. Obtained results agree with previous theoretical results using Liechtenstein's formula to calculate the exchange constants and the Monte Carlo simulation technique to estimate the Curie temperature.have studied the exchange constants for the stoichiometric Ni 2 MnGa alloys for three values of the c/a ratio (c/a = 0.95, 1 and 1.25) using Liechtenstein's formula [31,32] while Monte Carlo simulations have been employed to estimate a Curie temperature of 375 K for the cubic austenitic phase [33]. Recently, the same group of authors have studied the exchange constants for the off-stoichiometric alloys both in the austenitic and martensitic phases [34,35], while Ghosh and Sanyal have focused only in the austenitic phase [36].

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Oxalyl Chloride

Salmon¹

2001

Encyclopedia of Reagents for Organic Synthesis

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Photochemistry of .beta.-iodoacrylamides

Cited by 12 publications

References 8 publications

Approaches to the Synthesis of (±)-Strychnine via the Cobalt-Mediated [2 + 2 + 2] Cycloaddition: Rapid Assembly of a Classic Framework

Approaches to the Synthesis of (±)-Strychnine via the Cobalt-Mediated [2 + 2 + 2] Cycloaddition: Rapid Assembly of a Classic Framework

2,3,4,5-Tetrahydropyridine (Δ¹-piperideine) and its derivatives. Synthesis and chemical properties

Oxalyl Chloride

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Photochemistry of .beta.-iodoacrylamides

Cited by 12 publications

References 8 publications

Approaches to the Synthesis of (±)-Strychnine via the Cobalt-Mediated [2 + 2 + 2] Cycloaddition: Rapid Assembly of a Classic Framework

Approaches to the Synthesis of (±)-Strychnine via the Cobalt-Mediated [2 + 2 + 2] Cycloaddition: Rapid Assembly of a Classic Framework

2,3,4,5-Tetrahydropyridine (Δ1-piperideine) and its derivatives. Synthesis and chemical properties

Oxalyl Chloride

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2,3,4,5-Tetrahydropyridine (Δ¹-piperideine) and its derivatives. Synthesis and chemical properties