Synthetic Applications of Intramolecular Aza-Wittig Reaction for the Preparation of Heterocyclic Compounds

Abstract

A review focused on recent advances in intramolecular aza-Wittig reaction of phosphazenes with several carbonyl or analogous compounds is reported. Phosphazenes afford intramolecular aza-Wittig reaction with different groups within the molecule as aldehydes, ketones, esters, thioesters, amides, anhydrides and sulfimides. One of the most important applications of this reaction is the synthesis of a wide range of heterocyclic compounds, ranging from simple monocyclic compounds to complex polycyclic and macrocyclic systems.

One-pot, Three-component Synthesis of Fully Substituted 1,3,4-Oxadiazole Derivatives from (N-Isocyanoimino)triphenylphosphorane, Aromatic Carboxylic acids and (1R)-(-)-Campherchinon

“…Iminophosphoranes are important reagents in synthetic organic chemistry, especially in the synthesis of naturally occurring products, compounds with biological and pharmacological activity. 21,22 However, the organic chemistry of (N-isocyanimino)triphenylphosphorane 3 remains almost unexplored. (N-Isocyanimino)triphenylphosphorane 3 is expected to have synthetic potential because it provides a reaction system in which the iminophosphorane group can react with a reagent having a carbonyl functionality.…”

“…(N-Isocyanimino)triphenylphosphorane 3 is expected to have synthetic potential because it provides a reaction system in which the iminophosphorane group can react with a reagent having a carbonyl functionality. 21,22 In recent years, we have established a one-pot method for the synthesis of organophosphorus compounds. [23][24][25] In this paper, we report an interesting three-component reaction of (N-isocyanimino)triphenylphosphorane 3 (Scheme 1).…”

Preparation of Fully Substituted 1,3,4-Oxadiazole Derivatives from N-Isocyaniminotriphenylphosphorane, (E)-Cinnamic Acids, Chloroacetone and Primary Amines

“…Several interesting hetero-cyclization reactions involving iminophosphoranes have been reviewed. 7 These compounds can easily be converted through aza-Wittig reaction with isocyanates, carbon dioxide, or carbon disulfide into functionalized hetero-cumulenes which exhibit a rich chemistry of unusual synthetic promise. 7 The nucleophilicity at the nitrogen is a factor of essential mechanistic importance in the use of these iminophosphoranes as aza-Wittig reagents.…”

“…7 These compounds can easily be converted through aza-Wittig reaction with isocyanates, carbon dioxide, or carbon disulfide into functionalized hetero-cumulenes which exhibit a rich chemistry of unusual synthetic promise. 7 The nucleophilicity at the nitrogen is a factor of essential mechanistic importance in the use of these iminophosphoranes as aza-Wittig reagents. Iminophosphoranes are important reagents in synthetic organic chemistry, especially in the synthesis of naturally occurring products, compounds with biological and pharmacological activity.…”

“…N-isocyaniminotriphenylphosphorane 4 is expected to have synthetic potential because it provides a reaction system in which the iminophosphorane group can react with a reagent having a carbonyl functionality. 7,8 In recent years, we have established a one-pot method for the preparation of organophosphorus compounds.…”