First Electrophilic Substitution of (−)‐Agroclavine, Indoramine, Phenothiazine, Chlorpromazine, Iminodibenzyl, Imipramine, and Phenazone with Triethyl Orthoformate as an a1‐Synthon
- 1 January 1990
- journal article
- research article
- Published by Wiley in Archiv der Pharmazie
- Vol. 323 (7) , 439-442
- https://doi.org/10.1002/ardp.19903230712
Abstract
Agroclavine, imipramine hydrochloride, and phenazone reacted with triethyl orthoformate under acid catalysis in an electrophilic, tandem substitution reaction to furnish C3‐symmetrical tris(heteroaryl)methanes while indoramine, phenothiazine, and iminodibenzyl were formylated, ethylated, or ethoxymethylated. The ambident electrophilic reactivity of triethyl orthoformate as an a1‐synthon was clearly apparent.This publication has 5 references indexed in Scilit:
- The Reactions of Pindolol, Mepindolol, Carazolol, and Related Model Compounds with Triethyl Orthoformate: Pathways and Products of a New Colour ReactionArchiv der Pharmazie, 1990
- Ortho esters and dialkoxycarbenium ions: reactivity, stability, structure, and new synthetic applicationsChemical Society Reviews, 1987
- Dibenz[b,f]azepines and related ring systemsChemical Reviews, 1974
- SOME DERIVATIVES OF 10-ALKYLPHENOTHIAZINESThe Journal of Organic Chemistry, 1954
- Some Derivatives of PhenothiazineJournal of the American Chemical Society, 1944