Reference

Indenopyrazine and benzoquinoxaline intermediates

Indenopyrazine and benzoquinoxaline intermediates. Gaster, Laramie M.; Orlek, Barry S. (Beecham Group PLC, UK). U.S. US 4638066 A 20 Jan 1987, 20 pp. Division of U.S. 4,504,480. (United States of America) CODEN: USXXAM. CLASS: ICM: C07D241-38. ICS: C07D241-44; C07D241-42; C07D401-06. NCL: 544344000. APPLICATION: US 84-684080 20 Dec 1984. PRIORITY: GB 82-6558 5 Mar 1982; US 83-472218 4 Mar 1983. DOCUMENT TYPE: Patent CA Section: 28 (Heterocyclic Compounds (More Than One Hetero Atom)) Section cross-reference(s): 1 The title compds. trans-I [R1, R2 = H, alkyl, alkoxy, alkylthio, OH, halo, CF; R3 = CHO, (un)esterified CO2H, substituted Me; R4 = H, alkenyl, cycloalkyl, alkanoyl, esterified CO2H, (un)substituted alkyl, Ph, Bz, H2NCO, NH2, etc.; X = CH2CH2, CH2CO, COCH2, COCO; n = 1, 2] were prepd. as intermediates for the pentacyclic antidepressants trans-II (m = 1-3) or their N-oxides. trans-Et (1-chloro-2-indanyl)carbamate was aminolyzed with 2-H2NC6H4CO2Me to give 58% indandiamine trans-III (R3 = CO2Me, R4 = CO2Et). This was reduced with LiAlH4 to give 89% trans-III (R3 = HOCH2, R4 = Me) which was cyclocondensed with (BrCH2)2 to give 54% trans-I (R1 = R2 = H, R3 = HOCH2, R4 = Me, X = CH2CH2, n = 1). The latter was cyclized by heating at 80° in 88% H3PO4 to give 88% trans-II (R1 = R2 = H, R4 = Me, n = 1, m = 2) (IV). 38870-89-2 is just another one chemical used in this study. In mice IV inhibited behavioral symptoms induced by 5-methoxy-N,N-dimethyltryptamine with an ED50 of 8 mg/kg orally. IV also inhibited clonidine binding in rat brain synaptic membrane with Ki = 88 nM. .

Synthesis of quinazolines

Synthesis of quinazolines. Bergman, Jan; Brynolf, Anna; Elman, Bjoern; Vuorinen, Eino (Dep. Org. Chem., R. Inst. Technol.Some commonly used reagents like 38870-89-2 is used in this experiment., Stockholm S-100 44, Swed.). Tetrahedron, 42(13), 3697-706 (English) 1986. CODEN: TETRAB. ISSN: 0040-4020. DOCUMENT TYPE: Journal CA Section: 28 (Heterocyclic Compounds (More Than One Hetero Atom)) Reaction of RMgX (R = Me, Et, Ph, 4-MeC6H4, Me2CH, Bu; X = Cl, Br, iodo) with 2-H2NC6H4CN gave the intermediate 2-H2NC6H4CR:N- (I), which were cyclized to quinazolines by reaction with carbonyl compds. (e.g., acid chlorides, anhydrides, formates, and oxalates). Reaction of I with aldehydes, e.g. PhCHO, gave 1,2-dihydroquinazolines, which were readily dehydrogenated. Reaction of I with ClCO2Me gave 4-phenyl-2-quinazolinone, which was reduced to 3,4-dihydro-4-phenyl-2-quinazolinone by NaBH4 in AcOH. .