Angular substituents via cyclopropane derivatives of .beta.,.gamma.-unsaturated ketones

1969 ◽  
Vol 34 (3) ◽  
pp. 496-499 ◽  
Author(s):  
James J. Sims ◽  
V. K. Honwad
Keyword(s):  
Unsaturated Ketones ◽  
Derivatives Of ◽  
Cyclopropane Derivatives

ChemInform Abstract: Interaction of Derivatives of 7-Amino-1,5-benzodiazepin-2-ones with α,β-Unsaturated Ketones.

ChemInform ◽  
2011 ◽  
Vol 42 (17) ◽  
pp. no-no
Author(s):  
R. Janciene ◽  
Z. Stumbreviciute ◽  
A. Vektariene ◽  
R. Sirutkaitis ◽  
D. Podeniene ◽  
...  
Keyword(s):  
Unsaturated Ketones ◽  
Derivatives Of

Synthesis and Antitumor Activity of Cyclopropane Derivatives of Betulinic and Betulonic Acids

2005 ◽  
Vol 31 (3) ◽  
pp. 286-291 ◽  
Author(s):  
A. V. Symon ◽  
N. N. Veselova ◽  
A.P. Kaplun ◽  
N. K. Vlasenkova ◽  
G. A. Fedorova ◽  
...  
Keyword(s):  
Antitumor Activity ◽  
Derivatives Of ◽  
Cyclopropane Derivatives

THE ACTION OF SULPHURIC ACID ON CERTAIN DERIVATIVES OF CYCLOPROPANE

1933 ◽  
Vol 9 (2) ◽  
pp. 159-168 ◽  
Author(s):  
Charles F. H. Allen ◽  
Raymond Boyer
Keyword(s):  
Acetic Acid ◽  
Sulphuric Acid ◽  
Hydrogen Bromide ◽  
Cyclopropane Ring ◽  
Secondary Reaction ◽  
Derivatives Of ◽  
Cyclopropane Derivatives

A considerable variety of ketocyclopropanes has been submitted to the action of sulphuric acid, alone or in acetic acid. In general, the mode of reaction was similar to, though less drastic than, that of hydrogen bromide; this indicated a similar mechanism. When the cyclopropane ring was attacked, the product isolated was apparently formed by the addition of a molecule of water or acetic acid, or was the result of a secondary reaction dependent on a primary product so formed. The nitriles were hydrolyzed to amides without opening of the ring. A mechanism is suggested to account for the ring scission of cyclopropyl alcohols, which takes place in a different manner from most cyclopropane derivatives.

scholarly journals Branching out at C-2 of septanosides. Synthesis of 2-deoxy-2-C-alkyl/aryl septanosides from a bromo-oxepine

2012 ◽  
Vol 8 ◽  
pp. 522-527 ◽  
Author(s):  
Supriya Dey ◽  
Narayanaswamy Jayaraman
Keyword(s):  
Suzuki Reaction ◽  
Ring Expansion ◽  
Protecting Groups ◽  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Alkyl Aryl ◽  
Organometallic Reactions ◽  
Bond Forming ◽  
Derivatives Of ◽  
Cyclopropane Derivatives

This paper deals with the synthesis of 2-deoxy-2-C-alkyl/aryl septanosides. A range of such septanoside derivatives was synthesized by using a common bromo-oxepine intermediate, involving C–C bond forming organometallic reactions. Unsaturated, seven-membered septanoside vinyl bromides or bromo-oxepines, obtained through a ring expansion methodology of the cyclopropane derivatives of oxyglycals, displayed a good reactivity towards several acceptor moieties in C–C bond forming Heck, Suzuki and Sonogashira coupling reactions, thus affording 2-deoxy-2-C-alkyl/aryl septanosides. Whereas Heck and Sonogashira coupling reactions afforded 2-deoxy-2-C-alkenyl and -alkynyl derivatives, respectively, the Suzuki reaction afforded 2-deoxy-2-C-aryl septanosides. Deprotection and reduction of the 2-deoxy-2-alkenyl derivative afforded the corresponding 2-deoxy-2-C-alkyl septanoside free of protecting groups. The present study illustrates the reactivity of bromo-oxepine in the synthesis of hitherto unknown septanosides, branching out at C-2, through C–C bond formation with alkyl and aryl substituents.

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