Nucleophilic Addition of Amino-groups to an Activated Carbon–Carbon Double Bond

Abstract4-Pyrones bearing electron-donating and electron-withdrawing groups react with nonstabilized azomethine ylides to form pyrano[2,3-c]pyrrolidines in moderate to good yields. The reaction proceeds chemoselectively as a 1,3-dipolar cycloaddition of the azomethine ylide at the carbon–carbon double bond of the pyrone activated by the electron-withdrawing substituent. The reactivity of 4-pyrones toward azomethine ylides was rationalized by computational studies with the use of reactivity indexes. The pyrano[2,3-c]pyrrolidine moiety could be modified, for example by a ring-opening transformation under the action of hydrazine to provide pyrazolyl-substituted pyrrolidines.

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Substituent Effects on the Reactivity of the Silicon−Carbon Double Bond. Mechanistic Studies of the Ene-Addition of Acetone to Reactive Arylsilenes

Organometallics ◽

10.1021/om970875v ◽

1998 ◽

Vol 17 (4) ◽

pp. 645-651 ◽

Cited By ~ 11

Author(s):

Christine J. Bradaric ◽

William J. Leigh

Keyword(s):

Double Bond ◽

Substituent Effects ◽

Mechanistic Studies ◽

Carbon Double Bond ◽

Silicon Carbon ◽

Ene Addition

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Cycloaddition reactions across the carbon-carbon double bond of thiirene 1,1-dioxide

The Journal of Organic Chemistry ◽

10.1021/jo00181a040 ◽

1984 ◽

Vol 49 (7) ◽

pp. 1300-1302 ◽

Cited By ~ 16

Author(s):

Mitsuo Komatsu ◽

Yasuo Yoshida ◽

Masatoshi Uesaka ◽

Yoshiki Ohshiro ◽

Toshio Agawa

Keyword(s):

Double Bond ◽

Cycloaddition Reactions ◽

Carbon Double Bond

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ChemInform Abstract: Electrooxidative Fission of Carbon-Carbon Double Bond in a K2OsO2(OH)4/ HIO4 Double Mediatory System.

ChemInform ◽

10.1002/chin.199605042 ◽

2010 ◽

Vol 27 (5) ◽

pp. no-no

Author(s):

H. TANAKA ◽

R. KIKUCHI ◽

M. BABA ◽

S. TORII

Keyword(s):

Double Bond ◽

Carbon Double Bond

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Nucleophilic Addition of Amino-groups to an Activated Carbon–Carbon Double Bond

Reaction of lithium dimethylcuprate with (α-allenic carbonyl compounds: A 1,2-addition to the activated carbon—carbon double bond. Direct evidence for an α-cuprio ketone/copper enolate equilibrium

Nucleophilic addition of phenolate oxygen to an unactivated carbon-carbon double bond

Kinetics, mechanism, and reactivity of an activated carbon-carbon double bond in nitroxyl radicals and their diamagnetic analog in interaction with some secondary amines and polyethyleneimine

ChemInform Abstract: NUCLEOPHILIC ADDITION OF PHENOLATE OXYGEN TO AN UNACTIVATED CARBON-CARBON DOUBLE BOND

ChemInform Abstract: REACTION OF LITHIUM DIMETHYLCUPRATE WITH α-ALLENIC CARBONYL COMPOUNDS- A 1,2-ADDITION TO THE ACTIVATED CARBON-CARBON DOUBLE BOND. DIRECT EVIDENCE FO AN α-CUPRIO KETONE COPPER ENOLATE EQUILIBRIUM

RNA-Seq used to identify ipsdienone reductase (IDONER): A novel monoterpene carbon-carbon double bond reductase central to Ips confusus pheromone production

Reactions of 4-Pyrones with Azomethine Ylides as a Chemo­selective Method for the Construction of Multisubstituted Pyrano[2,3-c]pyrrolidines

Substituent Effects on the Reactivity of the Silicon−Carbon Double Bond. Mechanistic Studies of the Ene-Addition of Acetone to Reactive Arylsilenes

Cycloaddition reactions across the carbon-carbon double bond of thiirene 1,1-dioxide

ChemInform Abstract: Electrooxidative Fission of Carbon-Carbon Double Bond in a K2OsO2(OH)4/ HIO4 Double Mediatory System.

Reactions of 4-Pyrones with Azomethine Ylides as a Chemoselective Method for the Construction of Multisubstituted Pyrano[2,3-c]pyrrolidines