Dehydrothalicmine — A new base from Thalictrum isopyroides

DEHYDROTHALICMINE Thalictrum - A NEW BASE FROM isopyroides S. K h . M a e k h , V. G. Khodzhaev, a n d S. Y u . Y u n u s o v UDC 547.944/945 F r o m the benzene eluate obtained in the c h r o m a t o g r a p h y of the nonphenolic f r a c t i o n of the combined alkaloids f r o m the roots of T h a l i c t r u m i s o p y r o i d e s on a column of alumina we have isolated a c r y s t a l l i n e b a s e (I) with mp 190-191°C ( c h l o r o f o r m / e t h a n o l ) . The UV s p e c t r u m of (I) [kma x 267, 337 nm (log e 4.60, 3.93)] is c h a r a c t e r i s t i c f o r the dehydroaporphine b a s e s [1-3]. The IR s p e c t r u m of (I) has a strong band in the 1590-1640 c m -1 region and bands at 960 cm -1 (CH202) and 2845 c m - I (OCH3). The NMR s p e c t r u m of (I) (T scale) has a t h r e e - p r o t o n singlet at 7.04 ppm (N-CHz), a f o u r - p r o t o n multiplet in the 6.93-6.68 ppm region (2CH2) , singlets at 6.05 and 5.95 p p m (9H; 3OCH3), a t w o - p r o t o n singlet at 3.90 ppm (CH202) , and t h r e e o n e - p r o t o n singlets at 3.48, 3.02, and 1.72 ppm due to a r o m a t i c protons. The downfield shift of the signals of the N - C H 3 group and of the a r o m a t i c protons at Cll c o n f i r m s the dehydroaporphine s t r u c t u r e f o r (I) [1-3]. The m a s s s p e c t r u m of (I) shows the peak of the m o l e c u l a r ion with m / e 367 (100%) and a strong ( M - 1 5 ) peak. The ( M - l ) and ( M - 4 3 ) peaks c h a r a c t e r i s t i c of aporphine b a s e s a r e absent. Since the b a s e contains the s a m e substituents as t h a l i c m i n e (II) but differs f r o m it by two m a s s units, we a s s u m e that it is a dehydrothalicmine. A d i r e c t c o m p a r i s o n of Rf values and UV and IR s p e c t r a and a m i x e d melting point with an authentic s a m p l e identified (I) as the dehydrothalicmine obtained by the oxidation of (II) with p o t a s s i u m p e r m a n g a n a t e in acetonic solution. LITERATURE 1o 2. 3. CITED M. P. Cava, S. C. Havicek, A. Lindert, and R. J. Spandler, T e t r a h e d r o n Lett., 1966, 2937. H. G. Kiryakow and I. P. Pavlov, Chem. Ind. (London), 1968, No, 51 1807. M. P. Cava, V. Watanabe, K. Bessho, and M. L. Mitchell, T e t r a h e d r o n Lett., 1968, No. 20, 2427. O r d e r of the Red B a n n e r of L a b o r Institute of the C h e m i s t r y of Plant Substances of the A c a d e m y of Sciences of the Uzbek SSR. T r a n s l a t e d f r o m Khimiya Prirodnykh Soedinenii, No. 3, p. 381, M a y - J u n e , 1971. Original a r t i c l e submitted F e b r u a r y 19, 1971. © 1973 Consultants Bureau, a division of Plenum Publishing Corporation, 227 West 17th Street, New York, N. Y. 10011. All rights reserved. This article cannot be reproduced for any purpose whatsoeve.r without permission of the publisher. A copy of this article is available from the publisher for $15.00. 363  (...truncated)