TY - JOUR
AU1 - Bombarda, Carlo
AU2 - Erba, Emanuela
AU3 - Gelmi, Maria Luisa
AU4 - Pocar, Donato
AB - Ethyl 3‐benzoylamino‐2‐oxo‐6‐triphenylphosphoranylidenemethyl‐2H‐pyran‐5‐carboxylate (1) reacts with 2‐ nitrobenzaldehydes (2) to give 6‐(2‐nitrostyryl)‐2H‐pyran‐2‐ones (3), as the E stereoisomers, in good yields. The reduction of compounds 3, performed with hydrogen over Pd/C at room temperature and 1 atmosphere, leads to a mixture of 2‐amino‐4‐tetrahydroquinolinylidene‐2‐pentenedioic acid derivatives 5a‐d as the main products, the corresponding 3‐butenoic acid derivatives 6 and a minor amount of pyrano(2,3‐c)benzazocines 9a‐c. At 40 atmospheres and 90°, the reduction gives 4‐amino‐2‐tetrahydroquinolinylbutanoic acid derivatives 8a‐d as the main products and their precursors 7a,b,d as the minor ones. Amines 4c,d are isolated by stopping the reduction after the uptake of 3 equivalents of hydrogen.
TI - α‐Pyrones. II . Synthesis of tetrahydroquinoline derivatives of 4‐aminobutanoic and 2‐amino‐2‐pentenedioic acids
JF - Journal of Heterocyclic Chemistry
DO - 10.1002/jhet.5570290635
DA - 1992-10-01
UR - https://www.deepdyve.com/lp/wiley/pyrones-ii-synthesis-of-tetrahydroquinoline-derivatives-of-4-91ujbI1tls
SP - 1577
EP - 1581
VL - 29
IS - 6
DP - DeepDyve
ER -