ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Abnormal occurrence of the Bischler-Napieralski reaction

L. Dúbravková, I. Ježo, P. Šefčovič, and Z. Votický

Slovak Academy of Sciences, Bratislava

Abstract: It has been proven that the cyclodehydration of Et α-(3,4,5-trimethoxybenzamido)-β-(3,4-methylenedioxyphenyl)propionate (I) with P₂O₅ does not occur and with PCl₅, 4-piperonylidene-2-(3,4,5-trimethoxyphenyl)oxazolone, m. 198-200° (AcOH), is formed. With POCl₃ on I in boiling toluene is formed some 1 - (3,4,5 - trimethoxyphenyl) - 3 - carbethoxy - 6,7 - methylenedioxy-3,4-dihydroisoquinoline, m. 113-14° (EtOH) [picrate, m. 193-4° (EtOH)], and as a main product 5-ethoxy-4-piperonyl-2-(3,4,5-trimethoxyphenyl)oxazole, m. 98-9° (dil. EtOH).

Full paper in Portable Document Format: 119a536.pdf (in Slovak)

Chemical Papers 11 (9) 536–541 (1957)