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Volumn 41, Issue 20, 2002, Pages 3866-3870

A new method for the synthesis of nonsymmetrical sulfamides using Burgess-type reagents

Author keywords

Amines; Burgess reagents; Cyclization; Sulfamides; Synthetic methods

Indexed keywords

ALCOHOLS; AMINES; SYNTHESIS (CHEMICAL);

EID: 0037131479     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021018)41:20<3866::AID-ANIE3866>3.0.CO;2-T     Document Type: Article
Times cited : (42)

References (49)
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    • Amino alcohol substrates 14, 16, and 18 were prepared by the method of H. W. Heine, B. L. Kapur, J. L. Bove, R. W. Greiner, K. H. Klinger, C. Mitch, J. Am. Chem. Soc. 1954, 76, 2503. For alternative approaches to fashion these compounds, see J. T. Rudesill, R. F. Severson, J. G. Pomonis, J. Org. Chem. 1971, 36, 3071-3076.
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    • Amino alcohol substrates 14, 16, and 18 were prepared by the method of H. W. Heine, B. L. Kapur, J. L. Bove, R. W. Greiner, K. H. Klinger, C. Mitch, J. Am. Chem. Soc. 1954, 76, 2503. For alternative approaches to fashion these compounds, see J. T. Rudesill, R. F. Severson, J. G. Pomonis, J. Org. Chem. 1971, 36, 3071-3076.
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    • The literature pertaining to this field is so vast that it even has its own journal entitled Benzodiazepine. For additional general references, see information contained within: Comprehensive Medicinal Chemistry (Eds.: C. Hansch, P. G. Sammes, J. B. Taylor), Pergamon, Oxford, 1990.
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    • note
    • We would like to emphasize that all of our reported novel Burgess-type reagents (including 2 and 3) are readily isolable, can be purified through trituration with toluene, and then stored at 0°C for several months; the recent use of 3 in solution by a Merck group, therefore,[13d] should not be taken as a sign of instability in the solid form.
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    • note
    • 2 (60 psi), EtOH:EtOAc (4:1), 25°C, 24 h.[22] Subsequent alkylation was carried out by using a conventional protocol: sulfamide, NaH. DMF, 0°C to 25°C then alkyl halide, tetrabutylammonium iodide (cat), 25°C 4 h.[2d.5]


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