3768-70-5Relevant academic research and scientific papers
Azabicyclo[3.2.0]heptan-7-ones (carbapenams) from pyrrole
Gilchrist, Thomas L.,Lemos, Americo,Ottaway, Carol J.
, p. 3005 - 3012 (1997)
The azabicyclo[3.2.0]heptan-7-ones 4, 10, 16 and 24 have been prepared from pyrrole. The same general approach has been used for all these derivatives; namely, substitution of pyrrole at the 2- and 5-carbon atoms, catalytic hydrogenation to produce pyrrolidine-2-acetic acid derivatives, and cyclisation using tris(1,3-dihydro-2-oxobenzoxazol-3-yl)phosphine oxide 6. The catalytic hydrogenation of 2,5-disubstituted pyrroles gives only the corresponding cis-2,5-disubstituted pyrrolidines. The hydrogenation proceeds more easily when the nitrogen atom bears a tert-butoxycarbonyl substituent. The N-tert-butoxycarbonylpyrroles 8 and 21 bearing an α-substituent in the acetate side chain were hydrogenated with a high degree of facial stereoselectivity. This allowed the 6-phthalimidoazabicyclo-[3.2.0]heptan-7-one 24 to be isolated as a single diastereoisomer. The X-ray crystal structure of a precursor, the triester, 22a, has been obtained.
A new synthesis of versatile indolyl-3-carbonylnitriles
Veale, Clinton G.L.
, p. 5287 - 5290 (2015/08/26)
Abstract Indolyl-3-carbonylnitriles are compounds with demonstrated utility as intermediates in organic chemistry. However, their synthesis remains a challenge, requiring the use of toxic sources of cyanide, and often proceeding in low yields. Accordingly, presented here is a new synthesis of these versatile reactants, via dehydration of easily accessible α-oxoacetamides in generally high yields under simple reaction conditions.
Synthesis of Alkylpyrroles by the Sodium Borohydride Reduction of Acylpyrroles
Greenhouse, Robert,Ramirez, Coral,Muchowski, Joseph M.
, p. 2961 - 2965 (2007/10/02)
N-Unsubstituted alkylpyrroles are obtained by the reduction of the corresponding acylpyrroles with sodium borohydride in boiling 2-propanol.This reaction was demonstrated to proceed via the pyrrolylalkylcarbinol and was extended to the synthesis of a branched chain alkylpyrrole 25 from the tertiary alcohol 24.
