Bobbitt

The Bobbitt modification is the most widely used variation of the Pomeranz-Fritsch reaction. This modification involves cyclisation of benzylaminoacetal 10, usually prepared from the classical Pomeranz-Fritsch imine 9, to yield 4-hydroxy derivatives 11. The success of this method can be attributed to avoiding treatment and thus (partial) destruction of imine 10 under strongly acidic conditions. 

The Jackson modification involves cyclisation of iV-tosylated amine 12 and provides a complementary method to the classical Pomeranz-Fritsch reaction for entry into the fully unsaturated ring system 13. Amine 12 can be prepared from either the Pomeranz-Fritsch-Bobbitt imine 10 or reaction of benzylhalide 14 and the corresponding sodium anion 15. ... 

Hydroxyquinoline 28 was synthesized in excellent yield via cyclisation of the appropriate Pomeranz-Fritsch-Bobbitt imine 27. The desired amine 27 was prepared via hydride reduction of the classical Pomeranz-Fritsch imine. 

The Pomeranz-Fritsch-Bobbitt reaction has been utilized for the preparation of 4-hydroxy tetrahydroisoquinoline 31 in excellent yield. In this example 2,5-disubstituted benzaldehyde 29 has been successfully used as the reacting partner. 

Fritsch-Bobbitt reaction to synthesize tetrahydroisoquinoline portion Pomeranz-... 

Fritsch-Bobbitt imine 34 was prepared by reacting amine 33 with chiral epoxide 32. 

The Pomeranz-Fritsch-Bobbitt cyclisation of activated amino-acetal 38 yielded the desired 4-hydroxyquinoline 39 in acceptable yield. The non-obvious regioselectivity of the cyclisation can be attributed to the overriding para-directing effect of alkoxy groups. ... 

Treatment of substituted pyrollidinone 42 with a Lewis acid, rather than simple protic acid, lead to a Pomeranz-Fritsch-Bobbitt type condensation to yield indolizinone 43 as a single diastereomer. ... 

Although Edson2298 postulates that carbohydrates, as well as their derivatives are antiketogenic and compete with fatty acids for oxygen in the liver (as demonstrated by the Warburg technic), his results are only inferential since they are not based on the direct determination of the fatty acid decrease. Bobbitt and Deuel,82 on the other hand, found that not only was the formation of ketone bodies depressed when glycogen was added to the medium, but also that the disappearance of butyrate, as determined by direct analysis, was increased under such circumstances. 

Bobbitt, J.M. (1956) Periodate oxidation of carbohydrates. Adv. Carbohydr. Chem. 11, 1-41. 

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