filtrate. The solvent was removed in vacuo and the residue was purified by crystallization. NaBH4 reduction of 1-[3-(p-tolyl)-3-oxopropylamino] adamantane and subsequent treatment with HC1 yielded the corresponding alcohol hydrochlo,ide, mp 262-263", which did not give t,he correct elemental analysis even after repeated recrystallizations and whose ir spect,rum, however, left no doubt about its identity [vmnx (Nujol) 3375 (OH), 2700-2450 (PITH,+), and 1,590 em-' (aromatic)]. Condensation of this int,ermediat,e with toluene under FriedeLCrafts conditions produced readily the expected 3,3-ditolyl derivative. Friedel-Crafts Reaction.-To a suspension of the amino alcohol hydrochloride (1.0 mol) in about, ten times its weight of the appropriate aromatic hydrocarbon, anhydrous AlC18 ( 1.5 mol) was added in small portions and the reaction mixture was heated t,o 80-90", where it was kept for 30 min. Aft,er cooling to room t,emperatiire it was poured into a mixture of eqiial amounts of ice, TTIO, arid conceiitrated HCI. The prodiict, which separated ,talline form, was filtered OR' ntid purified by
Acknowledgment.-Adanmitatie a i d l-aIniii[,adarnaiitarie were prepared by Dr. >I. C. Bankiewicz.
B. 11. T. KEENEASD G. C. X\NXERING
EtOH and the precipitated acid (I, R1 = H, R2
= Me, Ra = C02H), mp ca. 350', was decarboxylated by heating with soda lime. The distillate gave Isas needles, mp 147-148' from EtOH. Anal. ( C ~ ~ H I I N C,) H. (5)
Uv spectrum closely aimilar to t h a t of t h e 11-inethyl isomer.
Substituted Quinazolone Hydrazides as Possible Antituberculous Agents SURENDR.4
s. PBRM.4R
AND
R. KCMAR
Department of Pharmacology and Therapeutics, King George's Medical College, Lucknow University, Lucknow-3, India J 1967 Iieceived J u ~ !10, The therapeutic use of isonicotinic acid hydrazide (isoiiiazid) and p-aminosalicylic acid (PAS) as antituberculous agents is well documented. A search for newer antituberculous compounds led us to synthesize some substituted quinazolone hydrazides having structural similarity t o PAS. Similar quinazolone hydrazides have also been shown to inhibit rat liver mitochondrial monoamine oxidase.'J Substituted quinazolone hydrazides were synthesized by the route outlined in Scheme I.
MetEway College of" Technology, Chatham, Ken[, England
SCHEME I
Receiaed January 8, 1968 Interest in the arititumour activity of ellipticine has prompted st,udieson isomeric systems.' Linear indenoquinolines are simple analogs of the corresponding pyridocarbazoles and we report here the synthesis for evaluation of the hitherto iinknown 6H-indeno[2,1-g]quinoline ( I , R1 = R 2 = R3 = H ) and some methyl homologs by the Skraup and Doebner procedures.
COOH
HINA C O O H
NH:
B' OH
/
R3
I Experimental Section Meltirig points were measured using an Electrothermal electrically heated block and are uncorrected. Uv spectra were measured in EtOH using Unicam SP500 and SP800B spectrophotometers. GH-Indeno[2,1-g]quinoline(I, R' = R2 = R3 = H).-A Skraup reaction on 3-fl~orenarnine~ with glycerol, 1 2 , and polyphosphoric acid a t 180" gave the parent indenoq~irioline,~ Anal. mp 142-143" (CsHs-petrOleUm ether (bp SO-SO")). (C16&3) C, H. The picrate had mp 254-255" dec (from 2methoxyethanol). Anal. (Cz?H1INdOi)C, H . ll-Methyl-GH-indeno[2,1-g]quinoline(I, R1 = M e ; R2 = R3 = H), prepared similarly from 4-methyl-3-fluorenaminej2 formed needles, mp 120-121" (from EtOH). Anal. (C17HIaN) C, H. The picrate formed needles, mp 237" dec (from 2-methoxyethanol). Anal. (C2sH1BN4O7)C, H, N. 2-Methyl-GH-indeno[2,1-g]quinoline(I, R2 = M e ; R' = R3 = H).-3-Fluorenamine was refluxed with pyruvic acid in
OH
x, I11
(1) A. N. Fujiwara, E. AI. Bcton, and L. Goodman, J . M e d . Chem., 10, 126 (1967). (2) J. Davey, B. R . T. Keene, and G. C. Mannering, J . Chem. Soc., C, 120
(1967). (3) Other conditions ( e a . . t h e sulfomix procedure) offered no advantage. (4) Cyclization at C-2 rather t h a n C-4 is to be expected: t h e nature of the product is confirmed b y t h e close similarity of its uv spectrum [A,,,:ty 213, 262, 311, 327, a n d 312 ml.r (log 4.62, 4.68, 4.00, 4.12, and 4.26)] t o t h a t of t h e product of t h e following reaction, which can only be 11-methyl-6Hin~leno[2,l-g]qriinoline [Amax 211, 266, 313, 325, and 341 (log 1.60, 4.71, 1.08, -1.11, and 4.11)].
I
X'
N (1) S.S. Parmar and R. C. .bora, Can. J . Chem., 44, 2100 (1966). (2) S. S.Parmar and R. C. .%rora, J . Jfed. Chem., 10, 1182 (196;).
