Silyl radical initiated radical cascade addition/cyclization: synthesis of silyl functionalized 4H-pyrido[4,3,2-gh]phenanthridin-5(6H)-ones

A cyclization cascade initiated by the addition of a silyl radical to an electron-deficient carbon–carbon double bond of N-arylacrylamides, followed by intramolecular cyano group insertion and homolytic aromatic substitution has been reported.

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Construction of a 4H-pyrido[4,3,2-gh]phenanthridin-5(6H)-one skeleton via a catalyst-free radical cascade addition/cyclization using azo compounds as radical sources

Organic Chemistry Frontiers ◽

10.1039/c7qo00926g ◽

2018 ◽

Vol 5 (5) ◽

pp. 793-796 ◽

Cited By ~ 12

Author(s):

Chen Zhang ◽

Junxia Pi ◽

Shu Chen ◽

Ping Liu ◽

Peipei Sun

Keyword(s):

Free Radical ◽

Cascade Reaction ◽

Radical Addition ◽

Azo Compounds ◽

Aromatic Substitution ◽

Catalyst Free ◽

Homolytic Aromatic Substitution ◽

Radical Cascade

The new radical addition/cyano insertion/homolytic aromatic substitution cascade reaction initiated by the thermal homolysis of azo compounds under catalyst-free conditions produced polycyclic phenanthridine derivatives.

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

Insect Biochemistry and Molecular Biology ◽

10.1016/j.ibmb.2020.103513 ◽

2021 ◽

pp. 103513

Author(s):

Katherine E. Fisher ◽

Richard L. Tillett ◽

Misha Footohi ◽

Cody Caldwell ◽

Juli Petereit ◽

...

Keyword(s):

Double Bond ◽

Pheromone Production ◽

Rna Seq ◽

Ips Confusus ◽

Carbon Double Bond ◽

Double Bond Reductase

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

Synthesis ◽

10.1055/s-0040-1706032 ◽

2021 ◽

Author(s):

Dmitrii L. Obydennov ◽

Vyacheslav D. Steben’kov ◽

Konstantin L. Obydennov ◽

Sergey A. Usachev ◽

Vladimir S. Moshkin ◽

...

Keyword(s):

Double Bond ◽

Ring Opening ◽

Azomethine Ylides ◽

Azomethine Ylide ◽

Dipolar Cycloaddition ◽

Computational Studies ◽

Carbon Double Bond ◽

Reactivity Indexes ◽

Reaction Proceeds

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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Unusual carboncarbon double bond cleavage in thiophenohomotropone system promoted by ethanedithiol

Tetrahedron Letters ◽

10.1016/s0040-4039(00)88433-6 ◽

1982 ◽

Vol 23 (28) ◽

pp. 2859-2862 ◽

Cited By ~ 1

Author(s):

Bernard Hanquet ◽

Mohammed El Borai ◽

Roger Guilard ◽

Yves Dusausoy

Keyword(s):

Double Bond ◽

Bond Cleavage ◽

Carbon Double Bond

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Radiation-induced homolytic aromatic substitution. III. Hydroxylation and nitration of benzene

The Journal of Physical Chemistry ◽

10.1021/j100578a006 ◽

1975 ◽

Vol 79 (11) ◽

pp. 1067-1069 ◽

Cited By ~ 12

Author(s):

Manfred K. Eberhardt

Keyword(s):

Aromatic Substitution ◽

Homolytic Aromatic Substitution ◽

Radiation Induced

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Raman Spectra of Polyisoprene Rubbers

Rubber Chemistry and Technology ◽

10.5254/1.3547256 ◽

1970 ◽

Vol 43 (2) ◽

pp. 313-321 ◽

Cited By ~ 5

Author(s):

S. W. Cornell ◽

J. L. Koenig

Keyword(s):

Double Bond ◽

Raman Spectra ◽

Structure Type ◽

Peak Height ◽

Mixed Structure ◽

Carbon Double Bond

Abstract The Raman spectra of cis-1,4-, trans-1,4-, and 3,4-polyisoprene are presented, and the frequencies are classified by configurational structure type. The stretching frequency of the carbon-carbon double bond vibrations are used to describe structure content. Only Raman bands characteristic of total 1,4 content and total vinyl content can be observed. Tentative values of structure content determined by both peak height and peak area are presented for two mixed structure rubbers.

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ChemInform Abstract: Intramolecular Coupling of η2-Iminoacyl Groups at Group 4 Metal Centers: A Kinetic Study of the Carbon-Carbon Double-Bond-Forming Reaction.

ChemInform ◽

10.1002/chin.198826224 ◽

1988 ◽

Vol 19 (26) ◽

Author(s):

L. D. DURFEE ◽

A. K. MCMULLEN ◽

I. P. ROTHWELL

Keyword(s):

Double Bond ◽

Kinetic Study ◽

Metal Centers ◽

Bond Forming ◽

Group 4 ◽

Carbon Double Bond ◽

Group 4 Metal

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Silyl radical initiated radical cascade addition/cyclization: synthesis of silyl functionalized 4H-pyrido[4,3,2-gh]phenanthridin-5(6H)-ones

Construction of a 4H-pyrido[4,3,2-gh]phenanthridin-5(6H)-one skeleton via a catalyst-free radical cascade addition/cyclization using azo compounds as radical sources

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.

Unusual carboncarbon double bond cleavage in thiophenohomotropone system promoted by ethanedithiol

Radiation-induced homolytic aromatic substitution. III. Hydroxylation and nitration of benzene

Raman Spectra of Polyisoprene Rubbers

ChemInform Abstract: Intramolecular Coupling of η2-Iminoacyl Groups at Group 4 Metal Centers: A Kinetic Study of the Carbon-Carbon Double-Bond-Forming Reaction.

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