Thiazole 2-morpholino

Variously trisubstituted thiazoles were prepared by Ried and Kaiser by condensing PhNHCPh=NCSR with BrCH R, (Scheme 149), R = OEt, morpholino and Ri = 4-NO2C6H4, Ac, Bz, COjEt, CN, 4-PhCsH4CO, NO2, 4-NO2C6H4CO, 4-BrCgH4CO, COCHaBr yields ranged from 45 to 92% (811). 

Perfluoro-2-methyl-2-penten-3-yl isothiocyanate, which was prepared from perfluoro-2-methyl-2-pentene and KSCN in benzonitrile in high yield by direct substitution of fluorine, is a stable and versatile educt for heterocyclic synthesis. This a,p-unsaturated isothiocyanate reacted with enamines, such as 1-methylindole and 2-methyl-1-morpholino-l-propene, to yield 2-(l-methylindol-3-yl)-perfluro-4,5-dihydro-5,5-dimethyl-4-ethylidene-l,3-thiazole and its analogue in fair yield. [95H1015]... 

Zur Bildung von 2-Methylamino-4,5,6,7,8,9,10,11,12,l3-decahydro-(cyclododeca[d -l,3-thiazol aus Oxo-cyclododecan und 5-Amino-l-[(l-methyl-hydrazino)-thiocarbonyl]-3-morpholino-l,2,4-triazol vgl. Lit.1872. 

Unter ahnlichen Bedingungen (Methanol/Natriummethanolat) wird 4-Morpholino-2-phenyl-l,3-thiazol (HX = Morpholin Ar = C6H5) (Schmp. 78-80°) zu 80% erhalten. 

Methyl-benzolsulfonylamino )-5-( 2-morpholino-ethyliden)-4,5-dihydro-l,3-thiazol 73% ... 

Benzoyl-2,4-bis-[4-methoxy-phenyl]-l,3-thiazol(R =R2 = 4-OCHj—C6H5 R3 = CJ-I5)770 3,7 g (0,01 mol)4-Methoxy-N-(4-methoxy-a-morpholino-benzyliden)-thiobenzamidund 1,99 g(0,01 mol) oj-Brom-acetophe-non werden in 15 m/ Acetonitril gelost und anschlieBend mit 5 ml Triethylamin versetzt. Es wird kurz aufgekocht und nach dem Abkuhlen mit Wasscr vcrdunnt. Man saugt das farblose Endprodukt ab und kristallisiert aus Ethanol um Ausbeute 3,58 g (89%) Schmp. 149-150". 

Amino-5-aminocarl)onyl-2-morpholino-l,3-thiazol (R1 =-N 0 X = NH2 I787 In eine Losung von 2,12g... 

Morpholino-4-(4-nItro-phenyl)-l,3-thiazol [R1 R2 = — (CH —O— (CH2)2— R3 = 4-N02—C R4 = H]826 Eine Losung von 2,22 g (0,01 mol) 4-Nitro-m-thioeyanat-acetophenon, 0,87 g Morpholin und 0,6 g Essig-siiure in 10 ml Ethanol wird 2 h unter RiickfluB erhitzt. Zur Ausfallung des Endproduktes wird portions-weise Wasser zugesetzt und gekiihlt. Es wird abgesaugt und aus verd. Ethanol umkristallisiert Ausbeute 2g (70%) Schmp. 142-143°. 

Brom-phenyl)-2-( 4-morpholino-1,3-butadienyl)-l, 3-thiazol 55% Schmp. 158-159 ... 

Cyan-2-(N-methyl-anilino)-4-methyl- 68 2-(Cyan-methyl)-4-hydroxy- 8, 10, 11 5-Cyan-2-methyl-4-phenyl- 152 5-Cyan-2-(4-methyl-phenyl)-4-trinuormethyl-a us 5-F1 uor-2-(4-methyl-phenyl)-4-trifl uor-methyl-1,3-thiazol/Kaliumcyanid 297 2-[l-Cyan-l-(methylthio-thiocarbouyl)-methyliden -4-pheny l-2,3-dihvdro- 233 5-Cyan-2-morpholino-4-phenyl- 136 2-[2-(3-Cyan-phenyl)-ethenyl]-4-isopropyl- 312... 

Type F Syntheses of Thiazoles (C-N-C-S + C). Substituted 7V-thiocarba-molyformamidines R CSN=CR NMe2 react with allyl bromide to give an azavinamidinium salt, which, upon treatment with a base, gives an ethylidene-A -thiazoline (R = = Me2N R = H, R = morpholino). This last com-... 

The 5-benzoyl-2-(2-morpholino-l-phenylethenyl)thiazole (286) reacts with phenacyl bromide at 170-200°C to give the trisubstituted pyrrolo[2,l-Z>]thiazoles (287) (Equation (29)) <88EGP262863>. 

OMe, or OH). A more efl cient approach to these 2-amino-heterocycles is the nitration of 2-dimethylamino(piperidino or morpholino)thiazoles, which proceeds in 70—75% yields. ... 

---