Journal
PURE AND APPLIED CHEMISTRY
Volume 89, Issue 3, Pages 367-377Publisher
WALTER DE GRUYTER GMBH
DOI: 10.1515/pac-2016-0907
Keywords
allene; allenylphosphine oxide; allenylphosphonate; benzofuran; chromene; cyclization; cycloaddition; ICPC-21; indolinone; quinoline
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Funding
- Council of Scientific and Industrial Research (CSIR)
- University Grants Commission [UGC-UPE-2]
- Department of Science and Technology
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In this paper, we review some of our results on cycloaddition and cyclization reactions of allenylphosphonates/and allenyl phosphine oxides. Thus nitro-substituted propargylic alcohols react with P(III)-Cl substrates to lead to unprecedented phosphono-benzazepines or -hydroxyindolinones. A similar reaction using a higher stoichiometry of P(III)-Cl precursor has led to the first observation of spontaneous resolution by crystallization in allene chemistry. In the reaction of these phosphorus based allenes with diphenyl isobenzofuran (DPBF), depending on the substituents, both [alpha, beta] and [beta,gamma]-cycloaddition products are formed. Extension of this work to sulfur based allenes and leading to a new [4+2] cycloadduct with DPBF is reported. A novel cyclization reaction of a functionalized allenylphosphine oxide with diethylamine leading to 3-diethylamino-4-diphenylphosphinoyl-1-naphthol is discovered. Base-catalyzed reactions of allenylphosphonates with 2-substituted benzaldehdes lead to novel thiochromans, chromenes, and quinolines. Allenylphosphonates undergo phosphonylation in the presence of tetrabutyl ammonium fluoride (TBAF). Vinyl azides derived from allenylphosphonates undergo thermolysis to form bis-phosphonopyrazines. [Pd]catalyzed reactions of allenes with 2-iodophenols, 2-iodobenzyl alcohol and 3-iodo-indole-2-carboxylic acids lead to a variety of benzofurans, benzopyrans and benzopyranones, respectively.
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