Kondensationsreaktionen von 3‐Methyl‐1‐phenyl‐pyrazolin‐(2)‐on‐(5) und dessen Derivaten

Abstract

1, R = COCH3) reagiert mit aromatischen Aldehyden zu den 4-Cinnamoyl-Derivaten 2 (Tab. l), mit aromatischen Aminen und mit Hydrazin zu den Imino-Verbindungen 3 (Tab. 2) bzw. 4. Aus 3-Methyl-1-phenyl-pyrazolon (1, R = H) und Natrium-[tc-anilino-benzyll-sulfonat entsteht das 4-[a-Anilino-benzyl]-Derivat 8, das auch aus dem 4-Benzyliden-pyrazolon 7 erhalten werden kann. 7 und Derivate addieren Nitroalkane zu den Verbindungen 9 (Tab. 4). Die Pyrano-pyrazol-Derivate 10-12 werden aus Pyrazolonen und P-Ketosaureestern hergestellt. 1 (R = H) kondensiert mit Acetoacetaniliden, rnit p-Tolyl-thiocarbaniliden und mit Thioacetamid zu den 4-substituierten Pyrazolonen 13 und 14; es 1aBt sich auch rnit Aryliden(bzw. Cycloalky1iden)-acetophenonen zu den Derivaten 15 umsetzen. Condensation Reactions of 3-Methyl-I-phenyl-2-pyruzolin-5-one and its Derivatives 4-Acetyl-3-methyl-l-phenyl-2-pyrazolin-5-one(1, R = COCH3) reacts with aromatic aldehydes to give the 4-cinnamoyl derivatives 2 (table 1). Condensation with aromatic amines and hydrazine 1 (R = COCH3) gives the imino compound 3 (table 2) and 4, respectively. The reaction of 3-methyl-1-phenylpyrazolone (1, R = H) with sodium tc-anilinobenzylsulfonate leads to 4-[tc-anilinobenzyl] derivative 8; this is also obtained from the 4-arylidenepyrazolone 7. The compound 7 and its derivatives add nitro alkanes, giving 9ad (table 4). Pyranopyrazole derivatives 10 -12 have been synthesized from pyrazolones and (3-ketocarboxylic esters. 1 (R = H) condenses with acetoacetanilides, with p-tolyl thiocarbanilide, and with thioacetamide to produce the 4-substituted pyrazolones 13 and 14. It has also been converted to the derivatives 15 by reaction with arylideneacetophenones.

Complete Catalytic Deoxygenation of CO2 into Formamidine Derivatives

“…Some heterocyclic compounds containing condensed pyrazoles such as pyrano[2,3‐ c ]pyrazoles possess a wide spectrum of pharmacological action, including analgesic, anti‐inflammatory, vasodilating and antihypertensive activities [19–21]. Hence, the preparation and biological properties of new substituted pyrano[2,3‐ c ]pyrazoles are of interest [22–36]. For these reasons, we focused our attention on the development of a new method for the preparation of pyrano[2,3‐ c ]pyrazoles starting from spirocyclopropanepyrazoles and now report the results of our investigation, a ring‐opening/cyanomethylation and intramolecular cyclization of them in the presence of a base such as sodium hydride.…”

On Efficient Synthesis, X‐Ray Analysis and DPPH Radical Scavenging Activity of Pyrazolone‐Based trans‐Chalcones

“…Piperidine was used as an organocatalyst for such condensation reactions before also. [31,32] The usage of microwave for efficient facile synthesis of trans-chalcones and preliminary antioxidant evaluation of synthesized compounds is the novelty of present work. To optimize the microwave assisted reaction conditions, model reaction (between 1 a and 2 b) was carried out in different solvents.…”

“…4‐Acetylpyrazolone 1 a was prepared via literature method and made to react with different commercially available aldehydes 2(a–m) . Piperidine was used as an organocatalyst for such condensation reactions before also …”

Spiro Heterocycles: Synthesis and Application of Spiro Pyrazol-3-one Derivatives

“…[38][39][40] Hence, the preparation and biological properties of new substituted pyrano [2,3-c]pyrazoles are interest. [41][42][43][44][45][46][47][48][49][50] To check something about reactivity of SPOs 2, we examined a ring transformation of SPOs 2a-d into pyrano [2,3-c]pyrazoles. 51 SPOs 2a-d were reacted with chloroacetonitrile in the presence of NaH 52 in DMF at 60 ˚C for 1 h to give the corresponding O-cyanomethylated pyrazoles 3a-d (Table 3, entries 1-4).…”