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- Title
Synthesis of (±)-Glaucine and (±)-Neospirodienone via an One-Pot Bischler—Napieralski Reaction and Oxidative Coupling by a Hypervalent Iodine Reagent.
- Authors
Wei-Jan Huang; Om V. Singh; Chung-Hsiung Chen; Shoei-Sheng Lee
- Abstract
Condensation of 3,4-dimethoxybenzeneethanamine (3d) and various benzeneacetic acids, i.e., 4ae, via a practical and efficient one-pot BischlerNapieralski reaction, followed by NaBH4 reduction, produced a series of 1-benzyl-1,2,3,4-tetrahydroisoquinolines, i.e., 5ae, in satisfactory yields (Scheme 3). Oxidative coupling of the N-acyl and N-methyl derivatives 6ae of the latter with hypervalent iodine ([IPh(CF3COO)2]) yielded products with two different skeletons (Scheme 4). The major products from N-acyl derivatives 6ac were (±)-N-acylneospirodienones 2ac, while the minor was the 3,4-dihydroisoquinoline 7. (±)-Glaucine (1), however, was the major product starting from N-methyl derivative 6e. Possible reaction mechanisms for the formation of these two types of skeleton are proposed (Scheme 5).
- Subjects
CONDENSATION; AMINES; CHEMICAL reduction; QUINOLINE
- Publication
Helvetica Chimica Acta, 2004, Vol 87, Issue 1, p167
- ISSN
0018-019X
- Publication type
Article