Preparation of Allenephosphoramide and Its Utility in the Preparation of 4,9-Dihydro-2H-benzo[f]isoindoles

Abstract

Allenephosphoramides were prepared from propargyl alcohols and diethyl arylphosphoramides using Yb(OTf)(3) as catalyst. In the presence of iodine, 4,9-dihydro-2H-benzo[f]isoindole derivatives could be efficiently constructed from the same two starting materials in a single step.

Recent Advances in the Synthesis of Heterocyclics via Cascade Cyclization of Propargylic Alcohols

“…In 2010, Wang's group accomplished an efficient approach for the construction of 4,9‐dihydro‐2 H ‐benzo[ f ]isoindole derivatives 110 in good yields via iodine‐promoted cascade cyclization of tertiary propargylic alcohols 108 with diethyl arylphosphoramides 109 as nucleophiles under mild conditions (Scheme 41). [57] In this transformation, the key intermediate phosphoramide substituted allene was generated, and then reacted with another propargylic alcohols to give the target product 110 . Experimental results showed that the phosphoramide substituted allenes C are unstable and could be easily hydrolyzed.…”

Molecular iodine-catalyzed multicomponent reactions: an efficient catalyst for organic synthesis

“…In the presence of iodine, 4,9-dihydro-2H-benzo[f]isoindole derivatives 141 could be efficiently constructed from propargyl alcohols and phosphoramides in the presence of iodine in a single step via ABB9 MCRs (Scheme 52). 117…”

Synthesis of dihydrobenzofurans and dihydroindoles by intramolecular Friedel-Crafts reaction of aryloxy- and arylamino-substituted propargylic alcohols

“…The allenes generated in situ could then undergo various cascade reactions to form many useful structural frameworks. [20][21][22][23][24][25][26] In a recent report, the Zhou group have developed an intramolecular Friedel-Crafts (IFC) reaction that provides a facile and versatile method for one-step construction Very recently, our group has reported the application of propargylic alcohols for the construction of substituted fluorenes, in which five-membered rings were constructed by IFC reactions. 29 It was envisaged that the similar IFC reaction of propargylic alcohols may also be applied to construct a five-membered heterocyclic skeleton.…”