Synthesis of Acyclic Nucleoside and Nucleotide Analogs Derived from 6-Amino-7H-purine-8(9H)-thione and 8-(Methylsulfanyl)adenine

2000 ◽  
Vol 65 (11) ◽  
pp. 1698-1712 ◽  
Author(s):  
Zlatko Janeba ◽  
Antonín Holý ◽  
Milena Masojídková
Keyword(s):  
Sulfur Atom ◽  
Sodium Methoxide ◽  
Potassium Hydroxide ◽  
Mitsunobu Reaction ◽  
Reaction Conditions ◽  
Nucleotide Analogs ◽  
Acyclic Nucleoside ◽  
Adenine Derivatives

Reaction of 8-bromoadenine derivatives 1 with thiourea in ethanol or butanol was used for the synthesis of the corresponding N9-substituted 6-amino-7H-purine-8(9H)-thiones 2. 8-(Methylsulfanyl)adenine derivatives 3 were prepared by reaction of thiones 2 with iodomethane in 1 M sodium methoxide or in aqueous 1.5 M potassium hydroxide. Alkylation of 6-amino-7H-purine-8(9H)-thione (2a) proceeds preferentially on the sulfur atom. Under similar conditions, alkylation of 8-(methylsulfanyl)adenine (3a) with diverse alkylation agents afforded N9-substituted adenine derivatives 3 and 6, and N3-substituted adenine derivatives 5 and 7. 8,3'-S-Anhydro derivatives 9 were prepared in good yields by cyclization of 6-amino-7H-purine-8(9H)-thiones 2d and 2f under the Mitsunobu reaction conditions.

Chlorination of Arylaldehyde-Derived Arylsulfonylhydrazones with N-Chlorosuccinimide Leading to 1,2,4,5-Tetrazine Derivatives

Synthesis ◽  
2019 ◽  
Vol 52 (01) ◽  
pp. 69-74
Author(s):  
Yuan-Zhao Ji ◽  
Hui-Jing Li ◽  
Ying Liu ◽  
Yan-Chao Wu
Keyword(s):  
Potassium Hydroxide ◽  
Reaction Conditions ◽  
Metal Free ◽  
Vinyl Halides

It has been reported previously that treatment of aryl­ketone-derived arylsulfonylhydrazones with NXS/(nBu)4NX affords exclusively vinyl halides. In contrast, we have found that treatment of aryl­aldehyde-derived arylsulfonylhydrazones with N-chlorosuccinimide in the presence of potassium hydroxide affords 1,2,4,5-tetrazine derivatives in good to excellent yields. The present reactions are carried out under metal-free and mild reaction conditions.

Preparation of YBa2Cu3O7−x precursors from a fused eutectic of sodium and potassium hydroxides

1989 ◽  
Vol 4 (6) ◽  
pp. 1307-1311 ◽  
Author(s):  
Nicholas Coppa ◽  
Daniel H. Nichols ◽  
John W. Schwegler ◽  
J. E. Crow ◽  
G. H. Myer ◽  
...  
Keyword(s):  
Thermal Decomposition ◽  
Potassium Hydroxide ◽  
Product Formation ◽  
Mechanical Grinding ◽  
Reaction Conditions ◽  
Fine Powders ◽  
Yttrium Barium ◽  
Sodium And Potassium

A method for preparing YBa2Cu3O7−x from the simultaneous thermal decomposition of the nitrates of yttrium, barium, and copper in an anhydrous fused eutectic of sodium and potassium hydroxide is described. This method eliminates the need for any mechanical grinding or the introduction of carbon containing anions. Products formed are fine powders (∼1 μm) having mole ratios 1.00Y:2.00Ba:3.06Cu.X-ray diffraction analyses reveal that the initial products are Y(OH)3, BaO2, and CuO, which when air calcinated/oxygen annealed at 900–950 °C form the superconducting YBa2Cu3O7−x A mechanism is postulated for product formation as a function of reaction conditions.

scholarly journals Facile synthesis of 1-alkoxy-1H-benzo- and 7-azabenzotriazoles from peptide coupling agents, mechanistic studies, and synthetic applications

2014 ◽  
Vol 10 ◽  
pp. 1919-1932 ◽  
Author(s):  
Mahesh K Lakshman ◽  
Manish K Singh ◽  
Mukesh Kumar ◽  
Raghu Ram Chamala ◽  
Vijayender R Yedulla ◽  
...  
Keyword(s):  
Amide Bond ◽  
Coupling Agents ◽  
Cyclic Ketones ◽  
Substitution Reactions ◽  
Facile Synthesis ◽  
Reaction Conditions ◽  
Peptide Coupling ◽  
Acyclic Nucleoside ◽  
Derivatives Of

(1H-Benzo[d][1,2,3]triazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), 1H-benzo[d][1,2,3]triazol-1-yl 4-methylbenzenesulfonate (Bt-OTs), and 3H-[1,2,3]triazolo[4,5-b]pyridine-3-yl 4-methylbenzenesulfonate (At-OTs) are classically utilized in peptide synthesis for amide-bond formation. However, a previously undescribed reaction of these compounds with alcohols in the presence of a base, leads to 1-alkoxy-1H-benzo- (Bt-OR) and 7-azabenzotriazoles (At-OR). Although BOP undergoes reactions with alcohols to furnish 1-alkoxy-1H-benzotriazoles, Bt-OTs proved to be superior. Both, primary and secondary alcohols undergo reaction under generally mild reaction conditions. Correspondingly, 1-alkoxy-1H-7-azabenzotriazoles were synthesized from At-OTs. Mechanistically, there are three pathways by which these peptide-coupling agents can react with alcohols. From 31P{1H}, [18O]-labeling, and other chemical experiments, phosphonium and tosylate derivatives of alcohols seem to be intermediates. These then react with BtO− and AtO− produced in situ. In order to demonstrate broader utility, this novel reaction has been used to prepare a series of acyclic nucleoside-like compounds. Because BtO− is a nucleofuge, several Bt-OCH2Ar substrates have been evaluated in nucleophilic substitution reactions. Finally, the possible formation of Pd π–allyl complexes by departure of BtO− has been queried. Thus, alpha-allylation of three cyclic ketones was evaluated with 1-(cinnamyloxy)-1H-benzo[d][1,2,3]triazole, via in situ formation of pyrrolidine enamines and Pd catalysis.

ChemInform Abstract: An Unexpected Migration of O-Silyl Group under Mitsunobu Reaction Conditions.

ChemInform ◽  
2011 ◽  
Vol 42 (38) ◽  
pp. no-no
Author(s):  
Ramu Sridhar Perali ◽  
Suresh Mandava ◽  
Venkata Rao Chunduri
Keyword(s):  
Mitsunobu Reaction ◽  
Reaction Conditions ◽  
Silyl Group

Nucleosteroids: Synthesis of Purinyl-Steroid Derivatives under Mitsunobu Reaction Conditions.

ChemInform ◽  
2005 ◽  
Vol 36 (27) ◽  
Author(s):  
Raul A. Cadenas ◽  
Maria E. Gelpi ◽  
Jorge Mosettig
Keyword(s):  
Mitsunobu Reaction ◽  
Reaction Conditions

Regiospecific O-alkylation of δ-tetronic acids under mitsunobu-reaction conditions

1990 ◽  
Vol 31 (48) ◽  
pp. 6973-6976 ◽  
Author(s):  
Joginder S Bajwa ◽  
Robert C Anderson
Keyword(s):  
Mitsunobu Reaction ◽  
Reaction Conditions

Oxidations of some α-amino acids under mitsunobu reaction conditions

1988 ◽  
Vol 29 (37) ◽  
pp. 4661-4664 ◽  
Author(s):  
Teodozyj Kolasa ◽  
Marvin J. Miller
Keyword(s):  
Amino Acids ◽  
Mitsunobu Reaction ◽  
Reaction Conditions

Introduction of a substituent at the 5″-position of N-Boc neomycin B under Mitsunobu reaction conditions

2005 ◽  
Vol 3 (11) ◽  
pp. 2064 ◽  
Author(s):  
Angelica Hernandez Linares ◽  
Dominique Fourmy ◽  
Jean-Louis Fourrey ◽  
Ali Loukaci
Keyword(s):  
Mitsunobu Reaction ◽  
Reaction Conditions ◽  
Neomycin B
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