63853-82-7Relevant academic research and scientific papers
Intramolecular [4+2] cycloaddition in n-allyl- and n-propargyl-α-furyl lactams
Poplevin, Dmitry S.,Nikitina, Eugeniya V.,Zaytsev, Vladimir P.,Varlamov, Alexey V.,Tilve, Santosh G.,Zubkov, Fedor I.
, p. 451 - 457 (2018/06/11)
The size of nitrogen heterocycle in N-allyl- and N-propargyl-α-furyl lactams, as well as the nature of the unsaturated substituent linked to the nitrogen atom affected the possibility of thermal intramolecular [4+2] cycloaddition between multiple bond and the furan ring. N-Allyl-γ-(α-furyl)butyrolactam was shown to be unreactive at temperatures from 140 to 230°С. Substituted δ-valero- and ε-caprolactams underwent partial Diels–Alder cyclization, forming tautomeric mixtures that contained both the initial open-chain form and the cyclic form (diastereomeric 3a,6-epoxyisoindoles fused with an aza ring) in ratios between 19:81 and 55:45. N-Propargyl-α-furyl lactams did not participate in thermal IMDAF reaction regardless of the ring size and the temperature of the synthesis.
Expedient pyrrolizidine synthesis by propargylsilane addition to N-acyliminium ions followed by gold-catalyzed α-allenyl amide cyclization
Breman, Arjen C.,Dijkink, Jan,Van Maarseveen, Jan H.,Kinderman, Sape S.,Hiemstra, Henk
supporting information; experimental part, p. 6327 - 6330 (2009/12/24)
(Chemical Equation Presented) A reaction sequence, involving the addition of (substituted) propargylsilanes to lactam-derived N-acyliminium ions followed by gold-catalyzed cyclization of the resulting α-allenyl amide, is applied in expedient syntheses of
A New -Type Annelation Useful for the Formation of Piperidine Skeletons
Shono, Tatsuya,Matsumura, Yoshihiro,Uchida, Kenshi,Kobayashi, Hidekazu
, p. 3243 - 3245 (2007/10/02)
A -type annelation between α,α'-dimethoxylated amides 4 and allyltrimethylsilane (5) gave piperidine derivatives 6.It was applied to the synthesis of piperidine, indolizidine, quinolizidine, 1-azabicycloundecane, 1-aza-8-oxabicyclononane, 8-azabicyclooctane, and 9-azabicyclononane derivatives.
Photolytic Dehydrochlorination of N-Chloro-N-alkyl Amides: Formaton of N-(α-Methoxyalkyl) Amides
Phan, Xuan T.,Shannon, Paul J.
, p. 5164 - 5170 (2007/10/02)
The photoinduced dehydrochlorination, in methanol, of N-chloro-N-alkyl amides with one substitient at the α position to nitrogen gave good yields of N-(α-methoxyalkyl) amides and the parent amides as secondary products.N-Chloro amides disubstituted at the α position gave mostly parent amides.In most cases no products resulting from 1,5 hydrogen transfer of amidyl radicals were observed.The quantum yields of decomposition of N-chloro-N-methylpentanamide (1a) were significantly greater than unity, indicative of a chain process for dehydrochlorination.The reaction was affected by the solvent, addition of base or radical inhibitors, concentration of N-chloro amide, light intensity, and irradiation wavelenght.
