3-ethoxycarbonyl-2-methyl-, ring synthesis

Thiophene, 2-amino-3-cyano-5-phenyl-synthesis, 4, 888-889 Thiophene, 3-amino-4,5-dihydro-cycloaddition reactions, 4, 848 Thiophene, 2-amino-3-ethoxycarbonyl-ring opening, 4, 73 Thiophene, 2-amino-5-methyl-synthesis, 4, 73 Thiophene, 2-anilino-synthesis, 4, 923-924 Thiophene, aryl-synthesis, 4, 836, 914-916 Thiophene, 2-(arylamino)-3-nitro-synthesis, 4, 892 Thiophene, azido-nitrenes, 4, 818-820 reactions, 4, 818-820 thermal fragmentation, 4, 819-820 Thiophene, 3-azido-4-formyl-reactions... 

Considerable synthetic use has been made of ethyl azidoformate. Typical reactions of this are the additions to double bonds as a path to aziridines. Thus addition of ethoxycarbonyl nitrene to l-ethoxy-2-methyl-l-trimethylsilyloxypropene affords the aziridine 612 that can be ring opened to yield (75%) the diester 613. Addition of the same nitrene to siloxydienes has also been reported One of the common reactions of ethoxycarbonyl nitrene is addition to arenes as a route to azepines. An example of this process is seen in the synthesis of the hexafluoroazepine 614 by addition of the nitrene to... 

Synthesis of pyrrol-2-yl acyclo C-nucleosides by forming the pyrrole ring onto the alditolyl chain was reported in 1922, when Pauly and Ludwig prepared 3-ethoxycarbonyl-2-methyl-2-(D-ara6mo-tetritol-l-yl) pyrrole (211), the first example of these compounds, by reaction of 2-amino-2-deoxy-D-glucose (210) with ethyl acetoacetate (22ZPC170) (Scheme 44). Since then, Spanish chemists have pioneered the synthesis of these compounds using this route and extensively studied their properties and mecha-... 

In the course of studies aimed at the development of a method for introducing substituents into the indole ring, Yokoyama et d. 61,62,65) succeeded in a simple synthesis of 4-bromodehydrotryptophan 131 by the vinylation of N-tosyl 4-bromoindole (124) in the presence of a stoichiometric amount of palladium salt Vinylation of fV-acetyldehydroalanine methyl ester 127 and N-(ethoxycarbonyl)dehydroalanine methyl ester 222 with 124 occurred in the presence of a stoichiometric amount of PdClj to give the corresponding 4-bromodehydrotryptophan 223 and 224, respectively. This result opened the route for a simple synthesis of tryptophan derivatives. Actual preparation of the 4-bromotryptophan 133 was achiev by the vinylation of 4-bromoindole 124 with the V-Boc-dehydroalanine methyl ester 130 in die presence of a stoichiometric amount of Pd(OAc)2. The literature conditions [1.0 equiv. of... 

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