Solid phase synthesis of 6-acylamino-1-alkyl/aryl-4-oxo-1,4-dihydrocinnoline-3-carboxamides

Sereni, Laura; Tatò, Marco; Sola, Francesco; Brill, Wolfgang K.‐D.

doi:10.1016/j.tet.2004.06.103

Cited by 6 publications

(5 citation statements)

References 34 publications

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“…Diethylmalonate was added to a freshly synthesized phenyl diazonium chloride, obtained by action of sodium nitrite on aniline hydrochloride, in the presence of sodium acetate in ethanol to give the malonate derivative 72, which was converted into its diacid analogue 73 by hydrolysis in aqueous NaOH. 32 In a one-pot procedure, the diacid 73 was quantitatively converted into diacyl chloride using thionyl chloride in 1,2-dichlorobenzene. After evaporation of the excess of thionyl chloride, and without isolation of the diacyl chloride intermediate, titanium tetrachloride was added to conclude the cyclization and to furnish the 4-oxo-1,4-dihydrocinnoline-3-carboxylic acid 74.…”

Section: Resultsmentioning

confidence: 99%

“…The cinnoline derivative 76 was obtained using a five-step synthetic route (Scheme ). Diethylmalonate was added to a freshly synthesized phenyl diazonium chloride, obtained by action of sodium nitrite on aniline hydrochloride, in the presence of sodium acetate in ethanol to give the malonate derivative 72 , which was converted into its diacid analogue 73 by hydrolysis in aqueous NaOH . In a one-pot procedure, the diacid 73 was quantitatively converted into diacyl chloride using thionyl chloride in 1,2-dichlorobenzene.…”

Section: Resultsmentioning

confidence: 99%

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Pharmacomodulations around the 4-Oxo-1,4-dihydroquinoline-3-carboxamides, a Class of Potent CB₂-Selective Cannabinoid Receptor Ligands: Consequences in Receptor Affinity and Functionality

et al. 2007

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CB2 receptor selective ligands are becoming increasingly attractive drugs due to the potential role of this receptor in several physiopathological processes. Thus, the development of our previously described series of 4-oxo-1,4-dihydroquinoline-3-carboxamides was pursued with the aim to further characterize the structure-affinity and structure-functionality relationships of these derivatives. The influence of the side chain was investigated by synthesizing compounds bearing various carboxamido and keto substituents. On the other hand, the role of the quinoline central scaffold was studied by synthesizing several 6-, 7-, or 8-chloro-4-oxo-1,4-dihydroquinolines, as well as 4-oxo-1,4-dihydronaphthyridine and 4-oxo-1,4-dihydrocinnoline derivatives. The effect of these modifications on the affinity and functionality at the CB2 receptor was studied and allowed for the characterization of new selective CB2 receptor ligands.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Pharmacomodulations around the 4-Oxo-1,4-dihydroquinoline-3-carboxamides, a Class of Potent CB₂-Selective Cannabinoid Receptor Ligands: Consequences in Receptor Affinity and Functionality

et al. 2007

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“…1093 The choice of such a solvent (which reduced the O-alkylated products) was based upon a previous paper by Chu and coworkers. 1094 N-Alkylation of cinnolines was conveniently performed in the solid phase by Sereni et al 1095 Although alkylation occurred at both the ring nitrogen atoms, only one product prevailed over a period of time.…”

Section: N-alkylation Of Heterocyclic Compounds (Excluding Nucleobases)mentioning

confidence: 99%

Mitsunobu and Related Reactions: Advances and Applications

et al. 2009

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His research interests include Organophosphorus Chemistry and Main Group Chemistry. He has over 115 publications so far and is a fellow of the Indian Academy of Sciences, Bangalore. N. N. Bhuvan Kumar was born in Cherukupalli, Guntur, India. After completing his B.Sc. from Nagarjuna University, he joined the School of Chemistry, University of Hyderabad, as a postgraduate student in the year 2000 and obtained his Master's degree in Chemistry. Currently, he is pursuing a Ph.D. on Organophosphonates under the supervision of Prof. K. C. Kumara Swamy. E. Balaraman was born in Kancheepuram, Chennai, India, in 1980. He received his M.Sc. in Chemistry from Vivekananda College [Madras University (2002)] and his Ph.D. degree in the areas of organophosphonates and modified BINOLs under the guidance of Prof. K. C. Kumara Swamy. Presently he is a postdoctoral fellow with Professors David Milstein and Ronny Neumann at the Weizmann Institute of Science, Israel. K. V. P. Pavan Kumar was born in Hyderabad (Andhra Pradesh), India, in 1979. He obtained his B.Sc. (Chemistry Honors) and M.Sc. (Chemistry) degrees from Sri Sathya Sai Institute of Higher Learning, Puttaparthi, A.P., India. He obtained his Ph.D. degree under the guidance of Prof. K. C. Kumara Swamy in October 2006. Presently he is working as a postdoctoral fellow in the area of hydroamination reactions using new titanium catalysts with Prof. Pierre Le Gendre at the Universite ´de Bourgogne, France.

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“…193 Finally, examples of alkylations of resin-bound nitrogencontaining functionalities (e.g., carbamates, hydroxyamines and amides) with halides have been reported. [194][195][196][197][198]…”

Section: Halogen Displacementmentioning

confidence: 99%

N-Alkylation Reactions and Indirect Formation of Amino Functionalities in Solid-Phase Synthesis

Olsen¹,

Franzyk²,

Jaroszewski³

2005

Synthesis

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Aliphatic and aromatic amino functionalities are present in a wide variety of natural products and drugs, as well as in synthetic small molecular probes with therapeutic and/or diagnostic potential in drug discovery. As solid-phase synthesis and combinatorial chemistry have emerged as important tools for generation of compound libraries, development of broad-scope and efficient chemistry for the introduction of various functional groups into resinanchored substrates is highly important. Herein, we present a review of the literature concerning formation of the amino functionality on solid phase.

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Solid phase synthesis of 6-acylamino-1-alkyl/aryl-4-oxo-1,4-dihydrocinnoline-3-carboxamides

Cited by 6 publications

References 34 publications

Pharmacomodulations around the 4-Oxo-1,4-dihydroquinoline-3-carboxamides, a Class of Potent CB₂-Selective Cannabinoid Receptor Ligands: Consequences in Receptor Affinity and Functionality

Pharmacomodulations around the 4-Oxo-1,4-dihydroquinoline-3-carboxamides, a Class of Potent CB₂-Selective Cannabinoid Receptor Ligands: Consequences in Receptor Affinity and Functionality

Mitsunobu and Related Reactions: Advances and Applications

N-Alkylation Reactions and Indirect Formation of Amino Functionalities in Solid-Phase Synthesis

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Solid phase synthesis of 6-acylamino-1-alkyl/aryl-4-oxo-1,4-dihydrocinnoline-3-carboxamides

Cited by 6 publications

References 34 publications

Pharmacomodulations around the 4-Oxo-1,4-dihydroquinoline-3-carboxamides, a Class of Potent CB2-Selective Cannabinoid Receptor Ligands: Consequences in Receptor Affinity and Functionality

Pharmacomodulations around the 4-Oxo-1,4-dihydroquinoline-3-carboxamides, a Class of Potent CB2-Selective Cannabinoid Receptor Ligands: Consequences in Receptor Affinity and Functionality

Mitsunobu and Related Reactions: Advances and Applications

N-Alkylation Reactions and Indirect Formation of Amino Functionalities in Solid-Phase Synthesis

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Product

Resources

About

Pharmacomodulations around the 4-Oxo-1,4-dihydroquinoline-3-carboxamides, a Class of Potent CB₂-Selective Cannabinoid Receptor Ligands: Consequences in Receptor Affinity and Functionality

Pharmacomodulations around the 4-Oxo-1,4-dihydroquinoline-3-carboxamides, a Class of Potent CB₂-Selective Cannabinoid Receptor Ligands: Consequences in Receptor Affinity and Functionality