Scope and Limitations of the T-Reaction

ISBN-13: 9783639032819 / Angielski / Miękka / 2008 / 204 str.

Constantin Rabong

Opis

The quinoline motif is an integral part of a wide variety of bioactive classes of compounds. An increasingly popular entry into tetrahydroquinolines is represented by the T-reaction, i.e. a subtype of the transformations relying on the isomerization-cyclization sequence known as the tert.-amino-effect. The latter was shown to proceed via a most remarkable helical dipolar intermediate generated upon a hydrideshift from an alpha-amino-C-H in tert.-anilines to an unsaturated ortho-substituent, accomplishing C-C-bond formation from a nonactivated NCH-moiety. The tert.-amino-effect was first brought to the attention of the synthetic community in the seminal contribution of O. Meth-Cohn and H. Suschitzky from 1972. Since then, the protocol has progressively evolved into a convergent, economical and yield-efficient preparation of structurally diverse, highly functionalized and pharmacologically valuable heterocycles, bearing stereoselectively introduced centers of chirality.

O autorze

Rabong, Constantin Constantin Victor Rabong was born in Vienna, Austria in 1982. In 2007, he gained his diploma in Technical Chemistry working in heterocyclic chemistry under the supervision of Prof. Ulrich Jordis at the Institute of Applied Synthetic Chemistry, Vienna University of Technology.