Some bisheterocycles having pyrrole and oxazoline/thiazoline units were synthesized from Z‐styrylsulfonylacetic acid methyl esters using samarium chloride.
A new class of thiadiazoles, triazoles and oxadiazoles were prepared from phenacylsulfonylacetic ester by protecting the carbonyl group by oximation. Deoximation was affected by using β‐cyclodextrin in the presence of an oxidizing agent.
A new class of spiro-pyrimidines, pyrazoles and isoxazoles are prepared by nucleophilic reaction of 3,5-diaroyl-2,6-diaryl-piperidine-4,4-dicarbonitrile (1), 3,5-diaroyl-2,6-diaryl-tetrahydropyran-4,4-dicarbonitrile (2) and 3,5-diaroyl-2,6-diaryl-tetrahydrothiopyran-4,4-dicarbonitrile (3) with urea, N,N'-dimethyl urea, thiourea, hydrazine hydrate and hydroxylamine hydrochloride.J. Heterocyclic Chem., 41, 951 (2004).In recent years we have been actively involved in the synthesis of spiro-heterocycles by the reaction of carbocycle-or heterocycle-1,1-dicarboxylic esters with various nucleophiles [1][2][3][4][5][6]. Prompted by the successful results on this front, we present in this article the utilization of compounds having gem-dicyano functionality in the synthesis of spiro-heterocycles by the cyclocondensation of former with various nucleophiles viz, urea, N,N′-dimethyl urea, thiourea, hydrazine hydrate and hydroxylamine hydrochloride.The 3,5-diaroyl-2,6-diaryl-piperidine-4,4-dicarbonitrile (1), 3,5-diaroyl-2,6-diaryl-tetrahydropyran-4,4-dicarbonitrile (2) and 3,5-diaroyl-2,6-diaryl-tetrahydrothiopyran-4,4-dicarbonitrile (3) are prepared by the reaction of 2,2-bis(1-benzoyl-2-phenyl-vinyl)-malononitrile with NH 4 OAc, P 2 O 5 and P 2 S 5 [7]. The cyclocondensation of 1, 2 and 3 with urea in the presence of NaOMe gave 1,5-diamino-7,11-dibenzoyl-8,10-diphenyl-2,4,9-triazaspiro[5.5]undeca-1,4-dien-3-one (4) 1,5-diamino-7,11-dibenzoyl-8,10-diphenyl-9-oxa-2,4-diazaspiro[5.5]-undeca-1,4-dien-3-one (5) and 1,5-diamino-7,11-dibenzoyl-8,10-diphenyl-9-thia-2,4-diazaspiro[5.5]undeca-1,4-dien-3-one (6). Similar reaction of 1, 2 and 3 with N,N′-dimethyl urea and thiourea afforded 7,11-dibenzoyl-1,5-diimino-2,4-dimethyl-8,10-diphenyl-2,4,9-triazaspiro[5.5]undecan-3-one (7), 7,11-dibenzoyl-1,5-diimino-2,4-dimethyl-8,10-diphenyl-9-oxa-2,4-diazaspiro[5.5]-undecan-3-one (8), 7,11-dibenzoyl-1,5-diimino-2,4-dimethyl-8,10-diphenyl-9-thia-2,4-diazaspiro[5.5]undecan-3-one (9) and 1,5-diamino-7,11-dibenzoyl-8,10-diphenyl-2,4,9-triazaspiro[5.5]undeca-1,4-dien-3-thione (10), 1,5-diamino-7,11-dibenzoyl-8,10-diphenyl-9-oxa-2,4-diazaspiro[5.5]undeca-1,4-dien-3-thione (11), 1,5-diamino-7,11-dibenzoyl-8,10-diphenyl-9-thia-2,4-diazaspiro[5.5]-undeca-1,4-dien-3-thione (12), respectively. Likewise, five membered spiro heterocycles, 1,4-diamino-6,10-dibenzoyl-7,9-diphenyl-2,3,8-triazaspiro[4.5]deca-1,3-diene (13), 1,4-diamino-6,10-dibenzoyl-7,9-diphenyl-8-oxa-2,3-diazaspiro[4.5]deca-1,3-diene (14), 1,4-diamino-6,10-dibenzoyl-7,9-diphenyl-8-thia-2,3-diazaspiro[4.5]deca-1,3-diene (15) and 4-amino-6,10-dibenzoyl-7,9-diphenyl-1-imino-2-oxa-3,8-diazaspiro[4.5]deca-3-ene (16), 4-amino-6,10-dibenzoyl-7,9-diphenyl-1-imino-2,8-dioxa-3-azaspiro[4.5]deca-3-ene (17), 4-amino-6,10-dibenzoyl-7,9-diphenyl-1-imino-2-oxa-8-thia-3-azaspiro[4.5]deca-3-ene (18) were prepared by refluxing 1, 2 and 3 with hydrazine hydrate and hydroxylamine hydrochloride, respectively (Scheme & Table 1). Though there is a possibility of diastereoisomers particularly in compounds 16-18...
and (XI) are prepared by cyclization of protected dithiocarbazide (V) followed by deoximation. -(PADMAVATHI*, V.; THRIVENI, P.; REDDY, B. C. O.; MAHESH, K.; J. Heterocycl. Chem. 44 (2007) 1, 93-98; Dep. Chem., Sri Venkateswara Univ., Tirupati 517 502, India; Eng.) -R. Staver 23-123
Ring closure reactions O 0130Synthesis of a New Class of Sulfone Linked Bisheterocycles. -SmCl3-promoted reaction between the amino alcohols/thiols (I) and the (Z)-styrylsulfonylacetic acid esters (II) is used as key step for the synthesis of the hitherto unknown title compounds (V). -(PADMAVATHI*, V.; REDDY, B. C. O.; MOHAN, A. V. N.; PADMAJA, A.; J. Heterocycl. Chem. 44 (2007) 2, 459-462; Dep. Chem., Sri Venkateswara Univ., Tirupati 517 502, India; Eng.) -H. Haber 31-030
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