Synthesis of several new isoxazole, imidazo[1,2-a]pyridine, imidazo[1,2-a]pyrimidine, benzoxadiazine and benzothiazine derivatives from hydroximoyl halides

Several new heterocyclic compounds such as 7‐substituted pyrazolo[1,5‐a]pyrimidine (5a–e) derivatives have been synthesized by the reactions of the versatile unreported sodium 3‐(4‐methyl‐2‐(4‐methylphenylsulfonamido)thiazol‐5‐yl)‐3‐oxoprop‐1‐en‐1‐olate (2) with amino heterocyclic (3a–e) derivatives. Reaction of (2) with hydrazonyl halide (7a–d) and hydroximoyl chloride (11a,b) derivatives followed by reaction with hydrazine hydrate afforded pyrazolo[3,4‐d]pyridazine and isoxazolo[3,4‐d]pyridazine derivatives, respectively incorporating a thiazole moiety have been described. All newly synthesized compounds were elucidated by considering the data of both elemental and spectral analysis.

Section: Methodsmentioning

confidence: 99%

Synthesis and Reactivity of 3‐oxoprop‐1‐en‐1‐olate Derivative as a Building Block for the Synthesis of Azole and Azine Derivatives

Khalil

Raslan

Sayed

2016

“…Elemental analyses were carried out at Microanalytical Center of the University of Cairo, Giza, Egypt. Hydrazonoyl halide and hydroximoyl halides were prepared as previously reported.…”

Section: Methodsmentioning

confidence: 99%

Useful Precursors for Synthesis of Some New Azolo[3,4‐d]pyridiazines, Azolo[1,5‐a]pyrimidines, Azolo[5,1‐c]triazines, Pyrazoles, and Benzo[b][l,4]diazepine

Abdelhamid

Fahmi

Baaiu

2015

Self Cite

Pyrazolo[3,4‐d]pyridazines, isoxazolo[3,4‐d]pyridazines, azolo[1,5‐a]pyrimidines, azolo[5,1‐c]triazines, pyrazoles, and benzo[b][l,4]diazepine were synthesized from the appropriate hydrazonoyl halides, hydroximoyl halides, heterocyclic amines, diazotized heterocyclic amines, arenediazonium chlorides, and o‐phenylenediamines with appropriate of sodium 3‐(5‐bromobenzofuran‐2‐yl)‐3‐oxoprop‐1‐en‐1‐olate or 1‐(5‐bromobenzofuran‐2‐yl)‐3‐(dimethylamino)prop‐2‐en‐1‐one. The newly synthesized compounds were elucidated by elemental analyses, spectral data, and alternative synthesis whenever possible.

“…3,6-Dichloro-2-(5-chlorothien-2-yl)imidazo [1,2-b]pyridazine (15) and 3,6-Dichloro-2-(thien-2-yl)imidazo [1,2-b]pyridazine (16).…”

Section: Experimental General Detailsmentioning

confidence: 99%

“…From the various reaction conditions available, we chose to use the N-chlorosuccinimide in chloroform media. In these conditions, the thienyl derivative (8) gave (15,16) identified by comparison with samples prepared above. Further confirmation was obtained using an unambiguous method.…”

Section: Introductionmentioning

confidence: 95%

Reactivity of 2‐substituted imidazo[1,2‐b]pyridazines: Preparation of 3‐nitro, nitroso and chloro derivatives

Hervet

Galtier

Enguehard

et al. 2002

The synthesis of 2‐substitutedimidazo[1,2‐b]pyridazines and their reactivity towards electrophilic substitutions are reported. The nitration was shown to be very dependent on the nature of the 2 substituent. Nitrosation using sodium nitrite in acetic acid media as a general method failed in all cases whereas chlorination was observed in warm hydrochloric acid. In order to ascertain the structure of some chloro derivatives, chlorination using N‐chlorosuccinimide was also reported. Depending of the nature of the substituent, the reaction occurred at the C‐3 imidazolic position and/or at the substituent on position 2. The 3‐nitroso‐2‐phenyl derivative was finally obtained using an alternative synthetic pathway by direct condensation of 3‐amino‐6‐chloropyridazine to ω‐chloro‐ω‐nitrosoacetophenone. The structural determinations were ascertained using high field lH and 13C‐NMR.