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Falcó, José Luis; Matallana, J. L.; Barberena, Jaume; Teixidó, Jordi; Borrell, José I.

doi:10.1023/a:1024830721010

Cited by 8 publications

(2 citation statements)

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“…512 The same group has also developed a procedure for solid-phase synthesis of ethers starting from N(fmoc),O(THP)-protected cis-hydroxyproline derivatives and 2-(3,5-dimethoxy-4-formylphenoxy) ethoxymethyl polystyrene (FDMP). 513 Other related applications include synthesis of (i) 2-substituted 4-aminopyrido[2,3d]pyrimidines (179) using etherified Wang resin (180), 514 (ii) tyrosine containing cyclic peptides using fmoc protected resin (181), 515 (iii) functionalized phenolic amino acids, 516 (iv) tellurium bound polymer with an ether linkage, 517 (v) polymer-supported chiral amines (e.g. 182) with ether linkages, 518 (vi) non-PEG derived polyether resins, 519 (vii) resin-bound aryl-cyclohexyl ethers (e.g.…”

Section: Etherification Without Cyclizationmentioning

confidence: 99%

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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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Section: Etherification Without Cyclizationmentioning

confidence: 99%

“…In the presence of pyridine • HF, the difluorophosphoranes, R 3 PF 2 (514) [R ) Ph, n-Bu, Me 2 N, MeO] have been isolated. These compounds are quite stable and can be isolated in good yields by using sonication (Scheme 150).…”

Section: Synthesis Of Fluorophosphoranesmentioning

confidence: 99%

Mitsunobu and Related Reactions: Advances and Applications

et al. 2009

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A Diversity‐Oriented, Microwave‐Assisted Synthesis of 4‐oxo and 4‐chloropyrido[2,3‐d]pyrimidin‐7(8H)‐ones

et al. 2004

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A microwave-assisted protocol for the synthesis of 4-oxo and 4-chloropyrido [2,3-d]pyrimidin-7(8H)-ones, 13 and 9 respectively, bearing a carbon substituent at C2 and a chlorine atom at C4 is reported. The introduction of a wide range of substituents at C2 renders this methodology easily amenable to combinatorial chemistry applications. Two examples of further derivatization of compounds 9, substitution by amine and Suzuki coupling, under microwave irradiation are also described. IntroductionPyrido [2,3-d] Our group has actively been working in the development of synthetic strategies for the preparation of 5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-ones (2) from a,b-unsaturated esters (3) (Scheme 1). Thus, in the so called cyclic strategy 2-methoxy-6-oxo-1,4,5,6-tetrahydropyridin-3-carbonitriles (5) are obtained by reaction of an a,b-unsaturated ester (3) and malononitrile (4, G CN) in NaOMe/MeOH [11]. Treatment of pyridones 5 with guanidine or amidine systems (6, R 5 NH 2 , H, alkyl, aryl, heteroaryl) affords 4-aminopyrido[2,3-d]pyrimidines (2, R 4 NH 2 ) [12]. The 1,5-dinitrile systems 7 were obtained by reaction of the corresponding pyridine-3-carbonitriles (5) with sodium cyanamide [13]. Treatment of 7 with hydrogen bromide afforded both positional bromo-substituted isomers depending on the thermal level employed. Thus, when the reaction was carried out at low temperature the 2-amino-4-bromo-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-ones (2, R 5 NH 2 , R 4 Br) were selectively formed, but when the process was run at high temperature the 4-amino-2-bromo-substituted compounds (2, R 5 Br, R 4 NH 2 ) were predominantly obtained [14]. This behaviour was found to be independent of the nature and position of the substituents present on the pyridone ring. On the other hand, we described an acyclic variation of the above protocol for the synthesis of pyridopyrimidines (2, R 4 NH 2 ) based on the isolation of the corresponding Michael adduct (8, G CN) [15], that also allowed us to obtain 4-oxopyrido [2,3-d] From the preceding discussion it is clear that, so far, we were only capable to synthesize 5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-ones (2) with a carbon substituent at position C2 by using an amidine (6), which causes the presence of an amino group or a carbonyl group at C4 of the resulting pyrido [2,3-d]pyrimidine. Now, as a part of our ongoing research in the area of combinatorial chemistry focused on the preparation of random libraries for High Throughput Screening (HTS), we decided to devise a strategy to synthesize 5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-ones (9) bearing a carbon substituent at C2 and a chlorine atom at C4 (R 4 Cl), susceptible of subsequent decoration chemistry (reduction, nucleophilic displacement with amines, C À C bond formation). The present paper deals with the results of this study. Results and discussionIn order to synthesize pyridopyrimidines (9) with a carbon substituent at position C2 and a chlorine atom at C4, we have developed a synthetic strategy based on the cyclization with anhydro...

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