Correction- Derivatives of Fluorene. XIII. Formation of 9-Arylimino Compounds in the Presence of Boron Trifluoride

1961 ◽  
Vol 26 (12) ◽  
pp. 5259-5259
Author(s):  
Murray Taylor ◽  
T Fletcher
Keyword(s):  
Boron Trifluoride ◽  
Derivatives Of

Aminocyclitols. II. Synthesis of thioanalogues of 2,5-dideoxystreptamine

1978 ◽  
Vol 56 (21) ◽  
pp. 2743-2749 ◽  
Author(s):  
Gerry Kavadias ◽  
Robert Droghini
Keyword(s):  
Thionyl Chloride ◽  
Boron Trifluoride ◽  
Protective Groups ◽  
Thiobenzoic Acid ◽  
Derivatives Of ◽  
L 13

N,N′-Dibenzoyl-2,5-dideoxystreptamine (8b) reacted with thionyl chloride to form the bisoxazoline 9 and the latter compound was treated with thiobenzoic acid to produce the dithiobenzoate 10a. Removal of the protective groups in 10a afforded (l,3/4,6)-4,6-diamino-1,3-cyclohexanedithiol (1) dihydrochloride. Reaction of 8b with triethyl orthoacetate in the presence of boron trifluoride yielded the monooxazoline 12 which, on reaction with thiobenzoic acid followed by deprotection of the resulting 13a, afforded (d,l)-(13/4,6)-4,6-diamino-3-hydroxycyclohexanethiol (2) dihydrochloride. Similarly, 3-N-benzoyl-1-N-ethoxycarbonyl-2,5-dideoxystreptamine (15) and l-N-benzoyl-3-N-ethoxycarbonyl-2,5-dideoxystreptamine (20) were converted via their respective oxazolines 17a and 22a, to the enantiomeric aminothiols 3 and 4. Protected derivatives of 1–4 are also described.

Chemistry of the Podocarpaceae. XX. Epoxides of ring-A-unsaturated 12-Methoxypodocarpa-8,11,13-trienes

1969 ◽  
Vol 22 (8) ◽  
pp. 1699 ◽  
Author(s):  
RC Canbie ◽  
WA Denny
Keyword(s):  
Boron Trifluoride ◽  
High Yield ◽  
Epoxide Ring ◽  
Oxidative Decarboxylation ◽  
Derivatives Of

Selective epoxidation of the methoxy alkene mixture (IX) from oxidative decarboxylation of 12-methoxypodocarpa-8,11,13-trien-19-oic acid (I) provides a method of obtaining a high yield of the exocyclic alkene (VII) from the mixture. Isolation of the 3α,4α-epoxide (X) during the epoxidation allows the formation of C 3 oxygenated derivatives of 12- methoxypodocarpa-8,11,13-trien-19-oic acid. ��� Methods for opening the epoxide ring of (X) and of the 4α,5α- and 4α,19-epoxides, (XI) and (XII), have been examined, and the structures of the products from rearrangement of each epoxide with boron trifluoride have been assigned.

General Method of Preparation of N-[(S)-(3-Hydroxy-2-phosphonomethoxypropyl)] Derivatives of Heterocyclic Bases

1993 ◽  
Vol 58 (5) ◽  
pp. 1151-1163 ◽  
Author(s):  
Petr Alexander ◽  
Antonín Holý
Keyword(s):  
Sodium Salt ◽  
Boron Trifluoride ◽  
Boron Trifluoride Etherate ◽  
Cesium Carbonate ◽  
Analogous Reaction ◽  
Sodium Salts ◽  
Heterocyclic Bases ◽  
Derivatives Of ◽  
General Method ◽  
Methanolic Ammonia

Reaction of (R)-1-O-p-toluenesulfonyl-1,2,3-propanetriol (IV) with N-trimethylacetylimidazole (II) afforded (R)-1-O-p-toluenesulfonyl-3-O-trimethyacetyl-1,2,3-propanetriol (V) which was reacted with dimethoxymethane in the presence of phosphorus pentoxide to give (R)-2-O-methoxymethyl-1-O-p-toluenesulfonyl-3-O-trimethyacetyl-1,2,3-propanetriol (VI). Compound VI was treated with acetic anhydride and boron trifluoride etherate and the obtained 2-acetoxy derivative VII reacted with bromotrimethylsilane to give the intermediary bromomethyl ether VIII. Compound VIII on reaction with tris(2-propyl) phosphite afforded (R)-2-O-bis(2-propyl)phosphonomethyl-1-O-p-toluenesulfonyl-3-O-trimethyacetyl-1,2,3-propanetriol (IX). Condensation of synthon IX with sodium salts of adenine, 2,6-diaminopurine, or with cytosine, 6-azacytosine or 2-chloroadenine in the presence of cesium carbonate, afforded fully protected diesters X and XIIIb which on methanolysis and reaction with bromotrimethylsilane gave N-[(S)-(3-hydroxy-2-phosphonomethoxypropyl)] derivatives of adenine (XIa), 2- chloroadenine (XIb), 2,6-diaminopurine (XIc), cytosine (XIVa) and 6-azacytosine (XIVb). In an analogous reaction, sodium salt of 4-methoxy-2-pyrimidone reacted with compound IX to give an intermediate XIIIa which on treatment with methanolic ammonia and subsequent deblocking under the same conditions also afforded the cytosine derivative XIVa. Sodium salt of 2-amino-6-chloropurine was in this way converted into the corresponding 2-aminopurine derivative XVIII. Deprotection of this compound gave 9-(S)-(3-hydroxy-2-phosphonomethoxypropyl)-2-aminopurine (XIX).

2-Acylated derivatives of ergoline

1982 ◽  
Vol 47 (6) ◽  
pp. 1757-1761 ◽  
Author(s):  
Jan Beneš ◽  
Jiří Křepelka
Keyword(s):  
Molecular Weight ◽  
Boron Trifluoride ◽  
Hypotensive Effect ◽  
Boron Trifluoride Etherate ◽  
Low Molecular Weight ◽  
Aliphatic Acids ◽  
Derivatives Of

Reactions of ergoline derivatives Ia-VIIa with anhydrides of low-molecular-weight aliphatic acids, catalysed by boron trifluoride etherate, gave 2-acylated derivatives Ib-Id, IIb-IId, IIIb-Vb, or 1,2-diacylated derivatives VIb and VIIb. The compound IIb exhibited a hypotensive effect.

ChemInform Abstract: BORON TRIFLUORIDE-CATALYSED REARRANGEMENTS OF SOME TETRASUBSTITUTED NEO-TRITERPENE EPOXIDES PART 4, DERIVATIVES OF A-NEOURSANE, A/B-NEOURSANE AND A/B-NEOLUPANE

1974 ◽  
Vol 5 (45) ◽  
pp. no-no
Author(s):  
SERGIO BERTOZZI ◽  
SERENA CATALANO ◽  
ANTONIO MARSILI ◽  
IVANO MORELLI ◽  
VALERIO SCARTONI
Keyword(s):  
Boron Trifluoride ◽  
Derivatives Of
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