The Reaction of Wittig-Horner Reagents and Phosphacumulenes With Nitrosonaphthol

Abstract

Wittig-Homer reagent l a reacts with 2-nitroso-I-naphthol 3 to give the olefinic adduct 5, the alkylated product 4 and the dimeric compound 6. When 2-nitroso-I-naphthol 3 reacts with Wittig-Homer reagents 1b.c. the corresponding phosphonate adducts 8a.b together with compounds 4 and 6 were obtained. Oxovinylidenetriphenylphosphorane 2 reacts with 3 to give the corresponding phosphoranylidenecyclobutylidene adduct 10 and triphenylphosphine oxide. The structural assignnlents of the new products are based on compatible analytical and spectroscopic results.Keywords: Wittig-Homer reagents (I-); phosphacumulene (2); 2-nitroso-1-naphthol 3; 'Ihe alkylaled product 4; the olefinic adducts 5; the dimeric product 6; the phosphonate adducts 8a, band the phosphonnylidene cyclobutylidene adduct 10

Antimicrobial activity of novel fused nitrogen, sulfur and phosphorus containing-heterocycles and relevant phosphonates with difurylpyridazine species

“…[30][31][32] Further intramolecular cyclisation of 9 afforded the phosphole 5 via the loss of ethanol molecule (Scheme 4). Regarding the observed N(2) alkylation by the Wittig-Horner (WH) reagent, it is a well established process, [33][34][35][36][37] and similar observation was previously reported in their reactions with pyrimidines, [14][15][16] pyrroles, 33 On the other hand, hydrolysis of the nitrile group and ring closure would lead to 4-iminothiopyran 21, which followed by hydrolysis to 4-thiopyranone 22. A similar transformation of an imino-group to the corresponding carbonyl group, is known for other imino intermediates.…”

Design, Synthesis, and Antioxidant/Antidiabetic Activity of Nucleic Acid Bases Bearing FusedN,S-Heterocyclic Phosphor Esters

“…The tendency of the intramolecular cyclization and the double bond migration process in 4 and 5 evoked the formation of 9 . Considering the N ‐alkylation by the WHE reagent, an analogous process has been observed in the reactions of WHE synthons with quinonimines , nitrosonaphthol , pyrroles , and pyrimidines .…”

The Reaction of Wittig and Wittig-Horner Reagents and Alkyl Phosphites with 1,2-Naphthoquinone-1-benzimide

“…More than a decade ago, we have reported that Wittig reagents (1) react with o-quinone diimines (2) to the corresponding ylide-phosphorane adducts 3 [1]. Moreover, it is known that Wittig-Horner reagents (4) give phosphonate adducts 5 and the alkylated product 6 when reacted with 2 (Scheme 1) [2].…”