Premium
Iodocyclisation of 1,4‐Dihydropyridines; Synthesis and Reactivity of 1‐Iodoindolo[2,3‐ a ]quinolizidines
Author(s) -
Lavilla Rodolfo,
Coll Oscar,
Nicolàs Marta,
Sufi Bilal A.,
Torrents Javier,
Bosch Joan
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199911)1999:11<2997::aid-ejoc2997>3.0.co;2-#
Subject(s) - chemistry , nucleophile , cyclopropane , reactivity (psychology) , moiety , substituent , stereochemistry , medicinal chemistry , ring (chemistry) , alkyl , organic chemistry , catalysis , medicine , alternative medicine , pathology
The addition of iodine (or related species) to β‐acyl‐ N ‐alkyl‐1,4‐dihydropyridines 1 , which possess an N ‐substituent with an appropriate nucleophile moiety, leads to the corresponding 3‐iododihydropyridinium ions, which undergo an internal nucleophilic attack to give, regio‐ and stereoselectively, the iodobi(poly)heterocyclic ring systems 2a – f in good yields. Reactivity studies on the iodoindoloquinolizidines 2e,f lead to the pentacyclic cyclopropane systems 4a,b , azides 5 and 6 , norderivative 9 and, by a base‐induced elimination, dihydropyridine 10 , a precursor of the zwitterionic alkaloids flavopereirine and 6,7‐dihydroflavopereirine.