Studies on the Heterocyclic Compounds. II. : On the Synthesis of Indolizine Derivatives

Ogata, Kanae

doi:10.1248/yakushi1947.89.7_1020

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1979

2005

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“…5-iodo-indolizines remain unknown. It is possible to introduce I or Br substituents at positions 1 or 3 by direct halogenation of 3- or 1-acylindolizines respectively [13,14]. It was shown that 1-bromo-2,3,7-trisubstituted indolizines may be converted to 1-iodoindolizine via 1-lithium derivative [15].…”

Section: Resultsmentioning

confidence: 99%

An Improved Synthesis of Some 5-Substituted Indolizines Using Regiospecific Lithiation

Кузнецов¹,

Буш²,

Рыбаков³

et al. 2005

Molecules

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Various 2-substituted indolizines can be directly and selectively lithiated in the 5 position and subsequent reactions with different electrophiles lead to some novel classes of indolizines. In particular, previously unknown 5-formyl- and 5-iodoindolizine have been prepared by this way and the molecular structure of 5-formyl-2-phenylindolizine was confirmed by X-Ray analysis. The reactivity of the 5-CHO- and 5-COPh groups toward some nucleophiles has been examined, and some additional classes of derivatives (oximes and alcohols) have been obtained. The possibility of Suzuki cross-coupling of 5-iodoindolizines and boronic acids was proven.

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Section: Resultsmentioning

confidence: 99%