Orthoamide und Iminiumsalze, LXXXI [1]. Orthoamid-Derivate der 1,3-Dimethylparabansäure / Orthoamides and Iminium Salts LXXXI [1]. Orthoamide Derivatives of 1,3-Dimethylparabanic Acid

2012 ◽  
Vol 67 (9) ◽  
pp. 907-912
Author(s):  
Willi Kantlehner ◽  
Erwin Haug ◽  
Christophe Bauer
Keyword(s):  
Hydrogen Chloride ◽  
Dimethyl Sulfate ◽  
One Pot ◽  
Sodium Methanolate ◽  
Iminium Salts ◽  
Iminium Salt ◽  
Amide Acetal ◽  
Derivatives Of ◽  
Subsequent Addition

1,3-Dimethyl-5-imino-imidazolidine-2,4-dione (7a) undergoes thiolysis (H2S) to give the corresponding imidazolidine-2,4-dione-5-thione derivative 6. The 5-N-methylimino analogue 7b can be obtained from 7a by methylation. Further methylation of 7b affords the crude iminium salt 8c from which the heterocyclic orthoamide derivatives 10, 11 can be prepared. The heterocyclic amide acetal 9a can be obtained from 7a and dimethyl sulfate in methanol and subsequent addition of sodium methanolate in a one-pot reaction. The aminal ester 10 is converted to the amide acetal 9a on treatment with hydrogen chloride in methanol

Preparation of Chloro and Sulfanyl Derivatives of 1-(2-Deoxy-4-C-hydroxymethyl-α-L-threo-Pentofuranosyl)uracil

1997 ◽  
Vol 62 (7) ◽  
pp. 1114-1127 ◽  
Author(s):  
Hubert Hřebabecký ◽  
Jan Balzarini ◽  
Antonín Holý
Keyword(s):  
Nucleophilic Substitution ◽  
Hydrogen Chloride ◽  
Thionyl Chloride ◽  
Sodium Methoxide ◽  
Thioacetic Acid ◽  
Uracil Derivatives ◽  
Derivatives Of ◽  
Hiv 1

3'-Chloro and 3'-acetylsulfanyl derivatives of 1-(2-deoxy-4-C-hydroxymethyl-α-L-threo-pentofuranosyl)uracil were prepared by reaction of 2,3'-anhydro-1-{5'-O-benzoyl-4'-C-[(benzoyloxy)methyl]-2'-deoxy-α-L-erythro-pentofuranosyl}uracil (3) with hydrogen chloride and thioacetic acid, respectively. The reaction with hydrogen chloride gave a mixture of N-1 and N-3 substituted uracil derivatives 12 and 14. Reaction of 1-{3-O-benzoyl-4-C-[(benzoyloxy)methyl]-2-deoxy-α-L-threo-pentofuranosyl}uracil (7) with thionyl chloride and subsequent debenzoylation afforded 1-(4-C-chloromethyl-2-deoxy-β-D-erythro-pentofuranosyl)uracil (19). Nucleophilic substitution with lithium thioacetate, followed by deacylation, converted 1-{3-O-benzoyl-4-C-[(benzoyloxy)methyl]-2-deoxy-5-O-p-toluenesulfonyl-α-L-threo-pentofuranosyl}uracil (9) into 1-(2-deoxy-4-C-sulfanylmethyl-β-D-erythro-pentofuranosyl)uracil (21). The obtained thiols were oxidized with iodine or air to give 1,1'-[disulfandiylbis(2,3-dideoxy-4-hydroxymethyl-α-L-threo-pentofuranose-3,1-diyl]di(pyrimidine-2,4-(1H,3H)-dione) (17) and 1,1'-[disulfandiylbis(2,5-dideoxy-4-hydroxymethyl-α-L-threo-pentofuranose-5,1-diyl]di(pyrimidine-2,4(1H,3H)-dione) (22). Reaction of 1-{3-acetylsulfanyl-5-O-methanesulfonyl-4-C-[(benzoyloxy)methyl]-2,3-dideoxy-α-L-threo-pentofuranosyl)}uracil (24) with methanolic sodium methoxide afforded 1-(3,5-anhydro-2,3-dideoxy-4-C-hydroxymethyl-3-sulfanyl-α-L-threo-pentofuranosyl)uracil (25). The same reagent was used in the preparation of 1-(3,5-anhydro-2-deoxy-4-C-hydroxymethyl-α-L-threo-pentofuranosyl)uracil (26) from 1-{4-C-[(benzoyloxy)methyl]-2-deoxy-5-O-p-toluenesulfonyl-α-L-threo-pentofuranosyl}uracil (8). From the series of 4'-substituted 2'-deoxyuridine derivatives, synthesized in this study, solely the 4'-chloromethyl derivative 19 and the oxetane derivative 26 exhibited an appreciable activity against HIV-1 and HIV-2.

ChemInform Abstract: One-Pot Synthesis of 1-Alkenyl Derivatives of Phospholane and Phosphinane - New Classes of Compounds.

ChemInform ◽  
2010 ◽  
Vol 33 (17) ◽  
pp. no-no
Author(s):  
Graziano Baccolini ◽  
Carla Boga ◽  
Rezio A. Buscaroli
Keyword(s):  
One Pot ◽  
One Pot Synthesis ◽  
Derivatives Of

A simple one-pot procedure for the iminium salt formation: an efficient route to β-arylethylamines

2005 ◽  
Vol 46 (9) ◽  
pp. 1471-1474 ◽  
Author(s):  
Yi-Yin Ku ◽  
Tim Grieme ◽  
Yu-Ming Pu ◽  
Ashok V. Bhatia ◽  
Steve A. King
Keyword(s):  
Salt Formation ◽  
One Pot ◽  
Iminium Salt ◽  
Efficient Route

scholarly journals The Reaction of Derivatives of D-Xylal and D-Arabinal with Hydrogen Chloride and Hydrogen Bromide.

1969 ◽  
Vol 23 ◽  
pp. 2083-2094 ◽  
Author(s):  
Klaus Bock ◽  
Inge Lundt ◽  
Christian Pedersen ◽  
Tord Holme ◽  
Alf A. Lindberg ◽  
...  
Keyword(s):  
Hydrogen Chloride ◽  
Hydrogen Bromide ◽  
Derivatives Of

scholarly journals One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates

2014 ◽  
Vol 10 ◽  
pp. 2981-2988 ◽  
Author(s):  
Joshua P Barham ◽  
Matthew P John ◽  
John A Murphy
Keyword(s):  
Visible Light ◽  
Tertiary Amines ◽  
One Pot ◽  
Carbon Nucleophiles ◽  
Iminium Salts ◽  
Iminium Ions ◽  
Nucleophilic Trapping ◽  
Limited Scope

Nucleophilic trapping of iminium salts generated via oxidative functionalisation of tertiary amines is well established with stabilised carbon nucleophiles. The few reports of organometallic additions have limited scope of substrate and organometallic nucleophile. We report a novel, one-pot methodology that functionalises N-substituted tetrahydroisoquinolines by visible light-assisted photooxidation, followed by trapping of the resultant iminium ions with organometallic nucleophiles. This affords 1,2-disubstituted tetrahydroisoquinolines in moderate to excellent yields.

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