ChemInform Abstract: Functionalized 2-Azabicyclo(3.3.1)nonanes. Part 17. Studies on the Synthesis of 8-Alkyl-8-aryl-2-azabicyclo(3.3.1)nonan-7-ones. A Short Synthetic Route to Functionalized 8-Alkyl Derivatives.

ChemInform ◽  
2010 ◽  
Vol 23 (32) ◽  
pp. no-no
Author(s):  
J. BONJOCH ◽  
N. CASAMITJANA ◽  
J. QUIRANTE ◽  
C. GARRIGA ◽  
J. BOSCH
2007 ◽  
Vol 48 (49) ◽  
pp. 8587-8589 ◽  
Author(s):  
Benoit Bachand ◽  
Mohamed Atfani ◽  
Bita Samim ◽  
Sophie Lévesque ◽  
Daniel Simard ◽  
...  

2010 ◽  
Vol 63 (12) ◽  
pp. 1656 ◽  
Author(s):  
Ernst Schaumann ◽  
Gerrit Oppermann ◽  
Michael Stranberg ◽  
Harold W. Moore

Two routes are reported for the synthesis of iminocyclobutenones having N-(het)aryl substitution: an addition/substitution sequence starting with cyclobutenediones and an aza-Wittig method. A new synthetic route to N-alkyl derivatives is also presented. This involves O-alkylation of 3-alkylamino-1,2-cyclobutenediones using Meerwein’s reagent and subsequent deprotonation under non-hydrolytic conditions. Lithium organyls were found to add to the remaining carbonyl group. The resulting tertiary alcohols undergo ring enlargement on heating in xylene to give 4-aminophenols, 4-amino-1-naphthols, or cyclopenta-annulated quinolines from 4-vinyl, 4-aryl, and 4-alkynyl derivatives, respectively.


Molecules ◽  
2020 ◽  
Vol 25 (10) ◽  
pp. 2377
Author(s):  
Agnieszka Wojtkielewicz ◽  
Damian Pawelski ◽  
Przemysław Bazydło ◽  
Aneta Baj ◽  
Stanisław Witkowski ◽  
...  

A concise synthesis of (16S,20S)-3β-hydroxy-5α-pregnane-20,16-carbolactam from tigogenin via the corresponding lactone is described. The most efficient synthetic route consisted of the lactone ring-opening with aminoalane reagent followed by PDC or Dess-Martin oxidation. The oxo-amide obtained was subjected to cyclization with Et3SiH/TFA or Et3SiH/Bi(TfO)3. Alternately, the lactone was converted first to the oxo-acid, which was then subjected to the microwave-assisted reductive amination. N-Alkyl derivatives were also obtained in a similar way.


Tetrahedron ◽  
1992 ◽  
Vol 48 (15) ◽  
pp. 3131-3138 ◽  
Author(s):  
Josep Bonjoch ◽  
Núria Casamitjana ◽  
Josefina Quirante ◽  
Carmer Garriga ◽  
Joan Bosch

ChemInform ◽  
2008 ◽  
Vol 39 (12) ◽  
Author(s):  
Benoit Bachand ◽  
Mohamed Atfani ◽  
Bita Samim ◽  
Sophie Levesque ◽  
Daniel Simard ◽  
...  

Author(s):  
Yamin Wang ◽  
Gareth Pritchard ◽  
Marc Kimber

Synthetic route for the synthesis of tetrasubstituted furan fatty acids; including experimental details, characterisation, and spectral data of all intermediates.


2018 ◽  
Author(s):  
Guangbin Dong ◽  
Renhe Li

Herein, we describe our initial development of an asymmetric Pd-catalyzed annulation between aryl iodides and racemic epoxides for synthesis of 2,3-dihydrobenzofurans using a chiral norbornene cocatalyst. A series of enantiopure ester-, amide- and imide-substituted norbornenes have been prepared with a reliable synthetic route. Promising enantioselectivity (42-45% ee) has been observed using the isopropyl ester-substituted norbornene (N1*) and the amide-substituted norbornene (N7*).


2020 ◽  
Vol 23 (23) ◽  
pp. 2598-2613
Author(s):  
Boris A. Zaitsev

: A retrospective view of exaltation of refraction observed for many unsaturated and aromatic compounds demonstrates that this physical phenomenon is undeservedly considered only as a qualitative measure of conjugation. This mini-review discusses numerous papers by the author that have been published earlier in inaccessible periodicals and collections of scientific papers. Using a great number of illustrations, the author shows that this parameter can be successfully used for quantitative estimate of resonance effects in organic and polymer chemistry. The methods for derivation of strictly additive atomic and group refraction constants are described; these constants were subsequently used as a tool that allowed quantitative estimation of resonance effects in mono-, di-, tri- and polyalkylbenzenes, alkylnaphthalenes, some alkyl derivatives of unsaturated hydrocarbons. These effects cause strictly fixed increase in refraction of carbon atoms in different structural modifications (graphene, fullerene, diamond) and in polycyclic aromatic hydrocarbons. The relevant results regarding quantitative estimation of degree of steric inhibition of resonance in sterically hindered ortho-dialkylbenzenes, 1,2,3- trialkyl-, 1,2,3,4-tetraalkyl-, and 1,2,3,4,5-polyalkylbenzenes accumulated by the author are summarized.


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