Self-condensation of an N-acyl-α-aminoketone to 2-(N-acylaminomethyl)pyrrole

SELF-CONDENSATION OF AN N-ACYL-a-AMINOKETONE TO 2- (N-.A CYLA MINOM ET HYL) PYRR O L E S. [. Zav'yalov, N. I. Aronova, and I. F. Mustafaeva UDC 542.953:547.447.5:547.74 For the first time we have observed the ability of an N-acyl-a-aminoketone to self-condense to 2- (N-acylami:aomethyl)pyrrole under the influence of an amine, enamine, or an a-amino acid. For example, treatment of N-acetylaminoacetone {I) with excess piperidine in the presence of molecular sieves or 1- piperidinocyclohexene in benzene (at 20 ~ for 150 h) and subsequent vacuum distillation at 3 mm gave ~40% of a mixture of 2-(N-acetylaminomethyl)--4-methylpyrrole (II) and its 1-acetyl derivatives (II1), the struc- tures of wb~:.ch were proved by elementary analysis, Erlich tests, the alkaline hydrolysis of III to II, as well as by the UV, IR, and PIV[R spectra. CH3 \ 2 CHaCONHCH2COCHa---~I II/CH2NHCOCHa (I) "~N / R R=H(II), CHACO (III) In its structural specificity, the conversion of I to II and III that we accomplished is similar to the biosynthesi~ of porphobilinogen from 5-aminolevulinic acid [1]. LITERATURE CITED 1. G. Bc~zold, G. Muller, and O. Muller, Angew. Chemie, 79, 905 (1967). N. ['. Zelinstdi Institute of Organic Chemistry, Academy of Sciences of the USSR. Translated from Izvestiya A~tdemii Nauk SSSR, Seriya Khimicheskaya, No. 7, p. 1674, July, 1972. Original article sub- mitted March 23, 1972. 1973 Consultants Bureau, a division of Plenum Publishing Corporation, 227 West 17th Street, New York, N. (. 10011. All rights reserved. This article cannot be reproduced for any purpose whatsoever without permission of the publisher. A copy of this article is available from the publisher for $15.00. 1625

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Transcript of Self-condensation of an N-acyl-α-aminoketone to 2-(N-acylaminomethyl)pyrrole

S E L F - C O N D E N S A T I O N O F A N N - A C Y L - a - A M I N O K E T O N E

T O 2 - (N-.A C Y L A M I N O M E T H Y L ) P Y R R O L E

S. [. Z a v ' y a l o v , N. I . A r o n o v a , a n d I . F . M u s t a f a e v a

UDC 542.953:547.447.5:547.74

Fo r the f i r s t t ime we have observed the abi l i ty of an N - a c y l - a - a m i n o k e t o n e to se l f -condense to 2- (N-acylami:aomethyl)pyrrole under the influence of an amine, enamine, or an a - a m i n o acid. For example, t r ea tmen t of N-ace ty laminoace tone {I) with excess piper idine in the p re sence of mo lecu la r s ieves or 1- p iper idinocyclohexene in benzene (at 20 ~ for 150 h) and subsequent vacuum dist i l la t ion at 3 m m gave ~40% of a mix tu re of 2 - (N-ace ty laminomethy l ) - -4 -me thy lpyr ro le (II) and i ts 1 -ace ty l de r iva t ives (II1), the s t r u c - tu res of wb~:.ch were proved by e l e m e n t a r y ana lys i s , Er l ich tes t s , the alkal ine hydro lys i s of III to II, as well as by the UV, IR, and PIV[R spec t ra .

CH3 \

2 CHaCONHCH2COCHa---~ I II/CH2NHCOCHa

(I) "~N / R

R=H(II), CHACO (III)

In i ts s t ruc tu ra l specif ic i ty , the convers ion of I to II and III that we accompl ished is s im i l a r to the biosynthesi~ of porphobil inogen f r o m 5-aminolevul inic acid [1].

L I T E R A T U R E C I T E D

1. G. Bc~zold, G. Muller , and O. Mul ler , Angew. Chemie , 79, 905 (1967).

N. [ ' . Zel instdi Inst i tute of Organic Chemis t ry , Academy of Sciences of the USSR. Trans la ted f r o m Izves t iya A~tdemi i Nauk SSSR, Seriya Khimicheskaya, No. 7, p. 1674, July, 1972. Original a r t i c l e sub- mit ted March 23, 1972.

�9 1973 Consultants Bureau, a division of Plenum Publishing Corporation, 227 West 17th Street, New York, N. (. 10011. All rights reserved. This article cannot be reproduced for any purpose whatsoever without permission of the publisher. A copy of this article is available from the publisher for $15.00.

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