ISSN:
0075-4617
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Syntheses with α-Metalated Isocyanides, XXXIII. - Chain Lengthening of Primary Amines via α-Metalated Isocyanides with Epoxides and Oxetane. New Synthesis of 3- and 4-Amino-alcohols, 5,6-Dihydro-4H-l,3-oxazines and 4,5,6,7-Tetrahydro-l,3-oxazepinesα-Lithiated isocyanides 5 react with epoxides to yield 3-hydroxyalkyl isocyanides 7, which on hydrolysis give 3-aminoalcohols, and on cyclization the oxazines 13. Reaction of 5b and d with oxetane yield 4-hydroxyalkyl isocyanides 11a and b, which can be hydrolyzed to 4-amino-alcohols or cyclized (albeit in poor yields) to the oxazepines 14.
Notes:
Die α-lithiierten Isocyanide 5 liefern mit Epoxiden 3-Hydroxyalkylisocyanide 7. Diese sind zu 3-Aminoalkoholen 9 hydrolysierbar oder zu den Oxazinen 13 cyclisierbar. Mit Oxetan reagieren 5b und d zu den 4-Hydroxyalkylisocyaniden 11a und b, die analog zu 4-Aminoalkoholen hydrolysierbar oder (wenngleich in schlechten Ausbeuten) zu Oxazepinen 14 cyclisierbar sind.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.197619761117
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