Protection of Amines by the Pyridine-2-sulfonyl Group and Its Cleavage under Mild Conditions (SmI2 or Electrolysis)

Goulaouic-Dubois, Catherine; Guggisberg, Armin; Hesse, Manfred

doi:10.1021/jo00123a041

Cited by 69 publications

(25 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…After hydrolysis of 8 with aqueous NaOH in EtOH, 9 was obtained in 65 YO yield with respect to 5. As the quantitative cleavage of the Ts group by electrolysis [23] has to be achieved before introduction of the phthaloyl group, the protecting group at N(4) has been exchanged for a Boc group (9 -+ 10 -+ 11). The primary alcohol derivative 11 was tosylated to obtain the precursor 12 for the Gabriel synthesis.…”

mentioning

confidence: 99%

Electrospray‐Ionization Mass Spectrometry. Part III. Acid‐Catalyzed Isomerization of N,N′‐Bis[(E)‐3‐(4‐hydroxyphenyl)prop‐2‐enoyl]spermidines by the Zip Reaction

Bigler

Schnider

et al. 1996

Helvetica Chimica Acta

Self Cite

View full text Add to dashboard Cite

show abstract

mentioning

confidence: 99%

Electrospray‐Ionization Mass Spectrometry. Part III. Acid‐Catalyzed Isomerization of N,N′‐Bis[(E)‐3‐(4‐hydroxyphenyl)prop‐2‐enoyl]spermidines by the Zip Reaction

Bigler

Schnider

et al. 1996

Helvetica Chimica Acta

Self Cite

View full text Add to dashboard Cite

show abstract

“…The electrochemical detosylation of 14 (400 mg) in EtOH soln. was performed according to [13]. The reaction was carried out under Ar at 58.…”

Section: Experimental Partmentioning

confidence: 99%

“…Fine colorless powder. IR (KBr): 3310m, 3263s, 2930m, 861m, 1643s, 1557m, 1428m, 1367w, 1305m, 1253w, 1189w, 1158s, 1088m, 1051w 13 3550m, 3287s, 2927m, 2881m, 1641s, 1598w, 1538m, 1494w, 1451w, 1427m, 1327s, 1154s, 1091s, 1039w, 968w, 907w, 856w, 13 3-[(4-Aminobutyl)amino]propanenitrile (25). To a soln.…”

Section: Experimental Partmentioning

confidence: 99%

“…The ester functionality in 7 furnished, after Cu(OAc) 2 -assisted aminolysis with excess putrescine (10), the amide 11, which itself could be easily tosylated to the ditosylprotected derivative 12, the definite ring precursor. Following ideas from the literature [8 ± 10], we decided to accomplish the ring closure using propane-1,3-diol bis(ptoluenesulfonate) (13), which was synthesized by a known procedure [11], and cesium carbonate as a base in DMF at elevated temperature. The two-fold substitution occurred smoothly under these conditions, enabling us to isolate the desired macrolactam 14 in 78% yield for the last step.…”

mentioning

confidence: 99%

“…1). Detosylation by a very well-established electrochemical method [12] [13] yielded the free spermidine macrolactam 15 after simple extractive workup (see Scheme 2).…”

mentioning

confidence: 99%

See 2 more Smart Citations

(−)-(3S)-3-(Tosylamino)butano-4-lactone, a Versatile Chiral Synthon for the Enantioselective Synthesis of Different Types of Polyamine Macrocycles: Determination of the Absolute Configuration of (−)-(R)-Budmunchiamine A

Detterbeck

Guggisberg

Popaj

et al. 2002

HCA

Self Cite

View full text Add to dashboard Cite

À)-(3S)-3-(Tosylamino)butano-4-lactone (1) and its derivative ethyl (À)-(3S)-4-iodo-3-(tosylamino)butanoate (2) are presented as easily accessible chiral building blocks for the construction of a range of different macrolactam frameworks important for the synthesis of naturally occurring polyamine alkaloids as well as for establishing a substance library of such compounds, including S-containing derivatives for biological tests. In addition to that, the absolute configuration of the spermine alkaloid (À)-(R)-budmunchiamine A (3) from Albizia amara was determined by total synthesis according to the new methodology.Scheme 2 a) PPh 3 , 1H-imidazole, I 2 , CH 2 Cl 2 , r.t., 1 h; 89%. b) t BuLi, Et 2 O, À 788 3 r.t., 2 h. c) CuBr ¥ Me 2 S, Et 2 O/THF, À 788 3À 208, 30 min. d) 2, Et 2 O/THF, À 608 3À 108, 3 h; 75%. e) H 2 N(CH 2 ) 4 NH 2 (10), Cu(OAc) 2 , r.t., 8 h; quant. f) TsCl, Et 3 N, CHCl 3 , r.t, 2 h; 93%. g) TsO(CH 2 ) 3 OTs (13), Cs 2 CO 3 , DMF, 658, 24 h, 78%.h) Electrolysis, EtOH, 58; 92%. Figure. ORTEP [14] Plot of the doubly N-tosylated macrolactam 14

show abstract

Labelling of Carbaboranyl Compounds with a Selenium Atom with a View to Applications in Boron-Neutron-Capture Therapy (BNCT) and Positron-Emission Tomography (PET)

Santos¹,

Argentini²,

Weinreich³

et al. 2000

HCA

View full text Add to dashboard Cite

We synthesized 2′‐carbaboranyl‐2,5′‐bi‐1H‐benzimidazoles containing 10 B‐atoms and labeled with Se or the positron‐emitting radionuclide 73Se (t1/2=7.1 h), with a view to their application to cancer treatment by boron‐neutron‐capture therapy (BNCT) and to compound‐distribution measurements in vivo by positron‐emission tomography (PET). Thus, 2,2′‐{{2′‐{4‐[1,2‐dicarba‐closo‐dodecaboran(12)‐2‐ylmethoxy]phenyl}‐[2,5′‐bi‐1H‐benzimidazol]‐5‐yl}imino}bis[ethanol] (26c) was obtained by the reaction of 2,2′‐[(3,4‐diaminophenyl)imino]bis[ethanol] (19) with ethyl 2‐{4‐[1,2‐dicarba‐closo‐dodecaboran(12)‐2‐ylmethoxy]phenyl}‐1H‐benzimidazole‐5‐carboximidate hydrochloride (25), as well as the analogues 26a and 26b (Scheme 6). Tosylation of compound 26c gave 4 regioisomers 27a – d, which, after selenation, produced 2′‐{4‐[1,2‐dicarba‐closo‐dodecaboran(12)‐2‐ylmethoxy]phenyl}‐5‐(tetrahydro‐2H‐1,4‐selenazin‐4‐yl)‐2,5′‐bi‐1H‐benzimidazole (29) in 42% yield (Scheme 7).

show abstract

Protection of Amines by the Pyridine-2-sulfonyl Group and Its Cleavage under Mild Conditions (SmI2 or Electrolysis)

Cited by 69 publications

References 0 publications

Electrospray‐Ionization Mass Spectrometry. Part III. Acid‐Catalyzed Isomerization of N,N′‐Bis[(E)‐3‐(4‐hydroxyphenyl)prop‐2‐enoyl]spermidines by the Zip Reaction

Electrospray‐Ionization Mass Spectrometry. Part III. Acid‐Catalyzed Isomerization of N,N′‐Bis[(E)‐3‐(4‐hydroxyphenyl)prop‐2‐enoyl]spermidines by the Zip Reaction

(−)-(3S)-3-(Tosylamino)butano-4-lactone, a Versatile Chiral Synthon for the Enantioselective Synthesis of Different Types of Polyamine Macrocycles: Determination of the Absolute Configuration of (−)-(R)-Budmunchiamine A

Labelling of Carbaboranyl Compounds with a Selenium Atom with a View to Applications in Boron-Neutron-Capture Therapy (BNCT) and Positron-Emission Tomography (PET)

Contact Info

Product

Resources

About