Ultrasound-Promoted One-Pot, Three-Component Synthesis of Spiro[indoline-3,1'-pyrazolo[1,2-b]phthalazine] Derivatives

Abstract

A series of 3'-aminospiro[indoline-3,1'-pyrazolo[1,2-b]phthalazine]-2,5',10'-trione derivatives have been synthesized by a one-pot three-component reaction of isatin, malononitrile or ethyl cyanoacetate and phthalhydrazide catalyzed by piperidine under ultrasound irradiation. For comparison the reactions were carried out under both conventional and ultrasonic conditions. In general, improvement in rates and yields were observed when the reactions were carried out under sonication compared with classical conditions.

An efficient approach to the synthesis of some novel heterocycles related to indoline moiety using [BMIm]Cl catalysis

“…As can be seen (Table 1) Table 2). The harsh reaction conditions, longer reaction times and irresability of other methods make our system a better choice [25][26][27][28][29].…”

CuII Anchored onto the Magnetic Talc: A New Magnetic Nanostructured Catalyst for the One‐Pot Gram‐Scale Synthesis of 1H‐Pyrazolo[1,2‐b]phthalazine‐5,10‐dione Derivatives

“…Synthesis of 1 H ‐pyrazolo[1,2‐b]phthalazine‐5,10‐diones via multicomponent reaction (MCRs) is a powerful tool due to its advantages of the intrinsic atom economy, simple procedure, structural diversity, energy saving, and reduced waste . To the best of our knowledge, there are only several works of literature about the multicomponent reactions of phthalhydrazide, malononitrile with aldehydes in the presence of diverse catalysts such as PTSA/[Bmim]Br, Et 3 N/EtOH, [Bmim]OH/MW, 1,8‐diazabicyclo[5,4,0]‐undec‐7‐en‐8‐ium acetate, DBU[CH 3 CO 2 ], Al‐KIT‐6, NiCl 2 .6H 2 O, InCl 3 , CuI NPs, TBBDA or PBBS, CAN PEG 400, Ni 0.5 Zn 0.5 Fe 2 O 4 nano‐crystallites, SBA@BiPy 2+ 2Cl − , RH@[SiPrDABCO@BuSO 3 H]HSO 4 , ZrO 2 NPs, PbO NPs, ZnO NPs, DCDBTSD, DMAP, β‐Cyclodextrin, NaHCO 3 , p ‐toluenesulfonic acid, and Fe 3 ‐ x Ti x O 4 @ SiO 2 @urea MNPs . Despite the merits of the previously reported synthetic methods, the generality of some of the known procedures is somewhat defected by using catalysts and solvents which are not acceptable in the context of green chemistry.…”

One-Pot Synthesis of 3-Functionalized 4-Hydroxycoumarin under Catalyst-Free Conditions

“…To date, GAP chemistry has been used in many asymmetric reactions [ 23 , 24 , 25 ] and MCRs [ 26 , 27 , 28 ]. As part of our current studies on the development of environmentally friendly routes to heterocyclic compounds [ 29 , 30 , 31 , 32 ], we now report an efficient and clean synthesis of 3-functionalized 4-hydroxycoumarin derivatives under catalyst-free conditions.…”