The Diels−Alder Reactions of Quinone Imine Ketals:  A Versatile Synthesis of Highly Substituted 5-Methoxyindoles

2001 ◽  
Vol 3 (21) ◽  
pp. 3325-3327 ◽  
Author(s):  
Scott C. Banfield ◽  
Dylan B. England ◽  
Michael A. Kerr
Keyword(s):  
Quinone Imine ◽  
Diels Alder

The Diels—Alder Reactions of Quinone Imine Ketals.

ChemInform ◽  
2004 ◽  
Vol 35 (33) ◽  
Author(s):  
Scott C. Banfield ◽  
Michael A. Kerr
Keyword(s):  
Quinone Imine ◽  
Diels Alder

ChemInform Abstract: The Diels-Alder Reactions of Quinone Imine Ketals: A Synthesis of the Ergot Skeleton.

ChemInform ◽  
2010 ◽  
Vol 32 (28) ◽  
pp. no-no
Author(s):  
Scott C. Banfield ◽  
Michael A. Kerr
Keyword(s):  
Quinone Imine ◽  
Diels Alder

ChemInform Abstract: The Diels-Alder Reactions of Quinone Imine Ketals: A Versatile Synthesis of Highly Substituted 5-Methoxyindoles.

ChemInform ◽  
2010 ◽  
Vol 33 (8) ◽  
pp. no-no
Author(s):  
Scott C. Banfield ◽  
Dylan B. England ◽  
Michael A. Kerr
Keyword(s):  
Quinone Imine ◽  
Diels Alder

The Diels-Alder Reactions of Quinone Imine Ketals: A Synthesis of The Ergot Skeleton

Synlett ◽  
2001 ◽  
Vol 2001 (03) ◽  
pp. 0436-0438 ◽  
Author(s):  
Scott C. Banfield ◽  
Michael A. Kerr
Keyword(s):  
Quinone Imine ◽  
Diels Alder

The Diels–Alder reactions of quinone imine ketals

2004 ◽  
Vol 82 (2) ◽  
pp. 131-138 ◽  
Author(s):  
Scott C Banfield ◽  
Michael A Kerr
Keyword(s):  
High Pressures ◽  
Ambient Pressure ◽  
Quinone Imine ◽  
Diels Alder

N-Benzoyl- and N-arylsulfonyl-p-benzoquinone-mono-imine ketals (QIKs) undergo smooth Diels–Alder cycloadditions with typical 1,3-butadienes to yield the expected endo adducts. Treatment with catalytic acid rapidly converts the adducts to dihydronaphthalenes. The N-benzoyl derivatives require high pressures for cycloadditions while the N-tosyl and N-nosyl derivatives proceed under thermal (ambient pressure) conditions. In all cases the cycloadditions are completely regioselective.Key words: Diels–Alder, quinone imine ketal, hyperbaric chemistry.

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