CS226940B1 - 1,2-dihydrofuro (2,3 to 4,5) pyrolo (1,2-d)-1,2,4-triazi-1-ones and method of preparing same - Google Patents
1,2-dihydrofuro (2,3 to 4,5) pyrolo (1,2-d)-1,2,4-triazi-1-ones and method of preparing same Download PDFInfo
- Publication number
- CS226940B1 CS226940B1 CS537482A CS537482A CS226940B1 CS 226940 B1 CS226940 B1 CS 226940B1 CS 537482 A CS537482 A CS 537482A CS 537482 A CS537482 A CS 537482A CS 226940 B1 CS226940 B1 CS 226940B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- dihydrofuro
- pyrrolo
- triazin
- ones
- pyrrole
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- SVMRIWUVQVPFTQ-UHFFFAOYSA-N 2h-pyrrolo[1,2-d][1,2,4]triazin-1-one Chemical compound O=C1NN=CN2C=CC=C12 SVMRIWUVQVPFTQ-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- QGJBRDAETPSJIU-UHFFFAOYSA-N 4h-furo[3,2-b]pyrrole-5-carbohydrazide Chemical class O1C=CC2=C1C=C(C(=O)NN)N2 QGJBRDAETPSJIU-UHFFFAOYSA-N 0.000 claims description 3
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 claims description 2
- MAYUCBCSAVDUKG-UHFFFAOYSA-N orthoacetic acid Chemical compound CC(O)(O)O MAYUCBCSAVDUKG-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 2
- HWZAVVUVDUMZAZ-UHFFFAOYSA-N C=1C=2NC(C(=O)NN)=CC=2OC=1C1=CC=CC=C1 Chemical class C=1C=2NC(C(=O)NN)=CC=2OC=1C1=CC=CC=C1 HWZAVVUVDUMZAZ-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 1
- 150000003920 1,2,4-triazines Chemical class 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- FQIAWPZQJCAPSW-UHFFFAOYSA-N 1h-pyrrole-2-carbohydrazide Chemical compound NNC(=O)C1=CC=CN1 FQIAWPZQJCAPSW-UHFFFAOYSA-N 0.000 description 1
- -1 2- (4-tolyl) -4H-furo [3,2-b] pyrrole 5- (4-tolyl) -1,2-dihydrofuran Chemical compound 0.000 description 1
- DTWJSNHSPVPQKW-UHFFFAOYSA-N 2-(4-methylphenyl)-4H-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound C1=CC(C)=CC=C1C(O1)=CC2=C1C=C(C(O)=O)N2 DTWJSNHSPVPQKW-UHFFFAOYSA-N 0.000 description 1
- FWGYRFWKBWPRJD-UHFFFAOYSA-N 4-methyl-2,3-dihydrofuran Chemical compound CC1=COCC1 FWGYRFWKBWPRJD-UHFFFAOYSA-N 0.000 description 1
- MMAIBGHDBYQYDI-UHFFFAOYSA-N 4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical class O1C=CC2=C1C=C(C(=O)O)N2 MMAIBGHDBYQYDI-UHFFFAOYSA-N 0.000 description 1
- CZRCFAOMWRAFIC-UHFFFAOYSA-N 5-(tetradecyloxy)-2-furoic acid Chemical compound CCCCCCCCCCCCCCOC1=CC=C(C(O)=O)O1 CZRCFAOMWRAFIC-UHFFFAOYSA-N 0.000 description 1
- ROYIFRBFJOAVNG-UHFFFAOYSA-N 5-oxa-1,10,11-triazatricyclo[6.4.0.02,6]dodeca-2(6),3,7,9,11-pentaene Chemical class O1C=CC2=C1C=C1N2C=NN=C1 ROYIFRBFJOAVNG-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Vynález sa týika l,2-dihydrofuro[2‘,3‘:4,5]pyrolo[l,2-d3-l,2,4-triazín-l-ónov a spůsobu ich přípravy.The present invention relates to 1,2-dihydrofuro [2,3-d: 4,5] pyrrolo [1,2-d3-1,2,4-triazin-1-one and a process for their preparation.
Jednou z metod přípravy zlúčenín s prikondenzovamým 1,2,4-triazínovým jadrom je realkcia dusíkových heterocyklov obsahujúcich v polohe 2 hydrazidoskupinu s octoestermi karboxylových kyselin [Monge Vega A., Aldana I., Rabbani Μ. M., Fernandes-Alvares E.: J. Heterocycl. Chem. 17,77 (1980)]. Z nich niektoré sú popísané ako biologicky účinné látky [Monge Vega A., Aldana I., Fernandes-Alvares E.: Eur. J. Med. Chem. 13, 573 (1978)]. Příprava hydrazídov kyselin fůro [ 3,2-b ] pyrol-5-karboxylových, vhodných medziproduktov na přípravu furo[2‘,3‘:4,5]pyrolo[l,2-d]-l,2,4-triazínov je popísané (autorské osvedčenie č. 226 929).One method of preparing compounds with a condensed 1,2,4-triazine nucleus is by realizing the nitrogen heterocycles containing the 2-position in the 2-position of the hydrazido group with octoesters of carboxylic acids [Monge Vega A., Aldana I., Rabbani Μ. M., Fernandes-Alvares, E .: J. Heterocycl. Chem. 17.77 (1980)]. Some of these are described as biologically active substances [Monge Vega A., Aldana I., Fernandes-Alvares E .: Eur. J. Med. Chem. 13, 573 (1978)]. Preparation of furo [3,2-b] pyrrole-5-carboxylic acid hydrazide acids, suitable intermediates for the preparation of furo [2 ', 3': 4,5] pyrrolo [1,2-d] -1,2,4-triazines are: described (author's certificate No 226 929).
1,2-Dihydrof uro [ 2‘,3‘ :4,5 ] pyrolo [1,2-d]-1,2,4-tríazín-l-Ďny, ktoré můžu slúžiť ako východzie zlúčeniny pre syntézu nových furokondenzováných heterocyklicikých zlúčenín .neboli doposial' připravené.1,2-Dihydrofuran [2 ', 3': 4,5] pyrrolo [1,2-d] -1,2,4-triazine-1-yne, which may serve as starting compounds for the synthesis of novel furocondensated heterocyclic compounds "not ready yet."
Predmetom ‘vynálezu sú 1,2-dihydrofuro- [2‘,3‘:4,5 ]pyrolo[ 1,2-d]-1,2,4-triazín-l-óny všeobecného vzorca IThe present invention provides 1,2-dihydrofuro [2, 3, 3: 4,5] pyrrolo [1,2-d] -1,2,4-triazin-1-ones of formula I
kdewhere
R je H, fenyl, 4-tolyl aR is H, phenyl, 4-tolyl and
R1 je H, CHs a spůsob ich přípravy.R 1 is H, CH 3 and a process for their preparation.
Podstata spůsobu přípravy 1,2-dihydrofurq[ 2*,3‘: 4,5 ] pyrolo [1,2-d ] -1,2,4-triazín-l-ónov vzorca I spočívá v tom, že sa na hydrazidy kyselin fůro [ 3,2-b ] pyrol-5-karboxylových všeobecného vzorca IIThe essence of the process for the preparation of 1,2-dihydrofuran [2 *, 3 ': 4,5] pyrrolo [1,2-d] -1,2,4-triazin-1-ones of the formula I is based on the formation of acid hydrazides furo [3,2-b] pyrrole-5-carboxylic acids of formula II
R %R%
NN
H C^NHNHZ (lil C ^ H NHNH Z (III
R má horeuvedený význam, •posobí trietylesterom kyseliny octomravčej alebo dctooetOvej v dimetylformamide pri teplote 100—153 °C.R is as defined above; it is triturated with triethylester or acetic acid in dimethylformamide at a temperature of 100-153 ° C.
Výhody spQjsoibu přípravy zlúčenín padla vynálezu spočívajú akrem iného, že sa reakcia uskutočnuje v jednom stupni v jednoduchej aparatúre s dobrými výťažkami.The advantages of the preparation of the compounds according to the invention are, besides others, that the reaction is carried out in one step in a simple apparatus with good yields.
1,2-Dihydrofuro[ 2‘,3‘: 4,5 ] pyr olo [ 1,2-d ] -1,2,4-triázín-l-óny majú široké použitie ako ireakčné komponenty v organickej syntéze, napr. reagujú s pentasulfidom fosforečným na korešpondujúce tióny, s trichlorldotm fosforečným na chlórderiváty a poskytujú možnost prifkondenzovania dalšieho heterocyklického kruhu.1,2-Dihydrofuro [2 ‘, 3‘: 4,5] pyrrolo [1,2-d] -1,2,4-triazin-1-ones are widely used as irrational components in organic synthesis, e.g. they react with phosphorus pentasulfide to the corresponding thions, with phosphorus trichlorodotrate to the chloro derivatives and provide the possibility of condensing another heterocyclic ring.
Predmet vynálezu ilustrujú, ale neobmedzujú následovně příklady:The invention is illustrated but not limited by the following examples:
Příklad 1Example 1
1,2-Dihýdrof uro [ 2‘, 3 ‘ :4,5 ] pyroloj 1,2-d ] -1,2,4-triazín-l-ón (la kde R = R1 = H)1,2-Dihdrofuran [2 ', 3': 4,5] pyrrole 1,2-d] -1,2,4-triazin-1-one (1a where R = R 1 = H)
Hydrazid kyseliny 4H-furo[3,2-b]pyrol-5-karhoxylovej (1,82 g, 0,011 mol) a trietylester kyseliny ortomravčej (2 g, 0,014 mol) v dímetylformajnide (10 ml) sa zahrieva pri teplote varu ipo dobu 2,5 h. Rozpúšťadlo sa vákuovo oddestiluje a zvyšok sa prekryštalizuje z dimetylformamidu.4H-Furo [3,2-b] pyrrole-5-carboxylic acid hydrazide (1.82 g, 0.011 mol) and triethyl orthoformate (2 g, 0.014 mol) in dimethylformajnide (10 ml) are heated at boiling point for a period of time. 2,5 h. The solvent was distilled off in vacuo and the residue was recrystallized from dimethylformamide.
Podobné sa z hydrazidů kyseliny 2-fenyl-4H-furo [ 3,2-b ] pyrol-5-karboxylovej připraví 7-fenyl-l,2-dihydrofuro[2‘,3‘:4,5]pyrolo[1,2-d]-1,2,4-triazín-l-ón (Ih kde R je fenyl, R1 = H) a z hydrazidů kyseliny 2-(4-tolyl)-4H-furo[ 3,2-b ]pyrol-5-karboxylovej sa připraví 7-(4-tolyl )-l,2-dihydrof uro [2‘,;3‘:4,5jpyrolof 1,2-d]-1,2,4-triazín-l-ón (Ic kde R je 4-tolyl, R1 = H).Similarly prepared from 2-phenyl-4H-furo [3,2-b] pyrrole-5-carboxylic acid hydrazides 7-phenyl-1,2-dihydrofuro [2 ', 3': 4,5] pyrrolo [1,2] d] -1,2,4-triazin-l-one (Ih wherein R is phenyl, R 1 = H) from the hydrazide of 2- (4-tolyl) -4H-furo [3,2-b] pyrrole 5- (4-tolyl) -1,2-dihydrofuran [2 ', 5-carboxylic acid ; 3 ': 4,5'-pyrrolof 1,2-d] -1,2,4-triazin-1-one (Ic wherein R is 4-tolyl, R 1 = H).
Příklad 2Example 2
4-Metyl-l,2-dihydrof uro [ 2‘,3‘:4,5 ] pyrolo[l,2-d-]-l,2,4-triazín-l-ón (Id kde R =' H, R1 = CH3)4-Methyl-1,2-dihydrofuran [2 ', 3': 4,5] pyrrolo [1,2-d] -1,2,4-triazin-1-one (Id where R = 'H, R 1 = CH 3)
Hydrazid kyseliny 4H-f uro [3,2-b ]pyrol-5karhoxylovej (1,82 g, 0,011 mol] a trietylester kyseliny ortoctovej (2 g, 0,012 mol) v dimetylformamide (10 ml) sa zahrieva pri teplote varu po dobu 2,5 h. Rozpúšťadlo sa •vákuovo oddestiluje a zvyšok sa prekryštaíizuje z dimetylformamidu. Podobné sa z hydrazidu kyseliny 2-feny l-4H-furo[ 3,2-b] pyrol-5-karboxylovej připraví 7-fenyl-4-metyl-l,2-dihydro [ 2*,3‘:4,5 ] pyrolo[ 1,2-d ] -1,2,4-triazín-l-ón (Ie kde R = fenyl, R1 = CH3) a z hydrazidů kyseliny 2-(4-tolyl)-4H-furo[3,2-b]pyrol-5-karboxylovej sa připraví 4-metyl-7- (4-tolyl) -1,2-dihy dro [ 2 ‘, 3 ‘: 4,5 ] pyrolo[ 1,2-d]-1,2,4-triazín-l-ón (If kde R =' 4-tolyl, R1 =' CH3). Štruktúra zlúčenín bola dokázaná elementárnou analýzou (tab. I) a IR, UV a 1H NMR spektraimi (tab. II a III). Spektrálné merania4H-Fluoro [3,2-b] pyrrole-5-carboxylic acid hydrazide (1.82 g, 0.011 mol) and triethyl orthoacetate (2 g, 0.012 mol) in dimethylformamide (10 ml) are heated at boiling point for 2 hours. The solvent was distilled off in vacuo and the residue was recrystallized from dimethylformamide and similarly prepared from 2-phenyl-4H-furo [3,2-b] pyrrole-5-carboxylic acid hydrazide 7-phenyl-4-methyl-. l, 2-dihydro- [2 *, 3 ': 4,5] pyrrolo [1,2-d] -1,2,4-triazin-l-one (Ie wherein R = phenyl, R 1 = CH 3) and hydrazides 2- (4-tolyl) -4H-furo [3,2-b] pyrrole-5-carboxylic acid prepared by 4-methyl-7- (4-tolyl) -1,2-dihydro [2 ', 3' : 4,5] pyrrolo [1,2-d] -1,2,4-triazin-l-one (If which R '4-tolyl, R1 =' CH 3). The structure of the compounds was shown by elemental analysis (Table I) and IR, UV and 1 H NMR spectra (Tables II and III)
Infračervené spektra sa namerali na spektrofotametri [SPECORD 71 IR (Carl Zeiss Jena)]. Elelktrónové spektrá sa namerali na spektrofotometr! [UV VIS (Carl Zeiss Jena)] v oblasti 200—800 nm pri koncentráciach 2 . ΙΟ-5—105 mol . I-1. XH NMR spektrá holi namerané na 80 MHz spektrometri [BS 487 C Tesla] v hexadeuterodimetylsulfoxide za použitia vnútorného štandardu hexametyldisiloxánu.Infrared spectra were recorded on a spectrophotometer [SPECORD 71 IR (Carl Zeiss Jena)]. The electron spectra were measured on a spectrophotometer! [UV VIS (Carl Zeiss Jena)] at 200-800 nm at concentrations of 2. ΙΟ- 5 —10 5 mol. I -1 . X H-NMR spectra obtained on stick 80 MHz spectrometer [Tesla BS 487 C] in hexadeuterodimethylsulfoxide using an internal standard of hexamethyldisiloxane.
Tabulka ITable I
1,2-Dihydrofuro[2‘,3‘:4,5]pyrolo( 1,2-d]-1,2,4-triazín-l-óny1,2-Dihydrofuro [2 ‘, 3‘: 4,5] pyrrolo (1,2-d) -1,2,4-triazin-1-one
228940228940
Tabulka IITable II
IČ a UV spektra zlúčenín Ia—If υ cm-1 λ—nmIR and UV spectra of Ia-If υ cm -1 λ-nm
XH NMR spektra zlúčenín Ia—If ffi X H NMR spectra of the compounds Ia-If ffi
Oí ee tí • I—<Oe ee t • I— <
>o <3 i-SM> o <3 i-SM
N cmN cm
CM~ wCM ~ w
ls cols co
CMCM
C/3 C/3 C/3 CM 00 CO CO CO^ CM* CM CM as aC / 3 C / 3 C / 3 CM 00 CO CO
xJDHB
CMCM
CM lsCM ls
Xll
CDCD
CO tsCO ts
XJ το Ό *d *3 T3 Xji r4 tS T-t O CM rd tJI CO rd IO.CO ts K ts C< ls lsXJ το d * d * 3 T3 Xj r4 tS T-t O CM rd tJI CO rd IO.CO ts K ts C <ls ls
Td xj T3 X3 XJ X$ XÍ XJ oco^iňoo Ή rd O rd rd O ists ls ls ls s tn w w irt rH co Cs ř^in co oo co o x o ·£ o o ta xj o Ό ω <wTd xj T3 X3 XJ X $ XÍ XJ oco ^ ň Ή rd O rd rd O ists ls ls ls s tn w w irt rH what Cs ^ ^ in what oo what about x o · £ o ta xj o Ό ω <w
M A Μ Μ Μ HM A Μ Μ Μ H
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS537482A CS226940B1 (en) | 1982-07-14 | 1982-07-14 | 1,2-dihydrofuro (2,3 to 4,5) pyrolo (1,2-d)-1,2,4-triazi-1-ones and method of preparing same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS537482A CS226940B1 (en) | 1982-07-14 | 1982-07-14 | 1,2-dihydrofuro (2,3 to 4,5) pyrolo (1,2-d)-1,2,4-triazi-1-ones and method of preparing same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS226940B1 true CS226940B1 (en) | 1984-04-16 |
Family
ID=5398527
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS537482A CS226940B1 (en) | 1982-07-14 | 1982-07-14 | 1,2-dihydrofuro (2,3 to 4,5) pyrolo (1,2-d)-1,2,4-triazi-1-ones and method of preparing same |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS226940B1 (en) |
-
1982
- 1982-07-14 CS CS537482A patent/CS226940B1/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Amr et al. | Synthesis, reactions, and anti-inflammatory activity of heterocyclic systems fused to a thiophene moiety using citrazinic acid as synthon | |
| Kalluraya et al. | Synthesis and pharmacological properties of some quinoline derivatives | |
| CA2258885A1 (en) | Tricyclic benzazepine vasopressin antagonists | |
| Peter | Adenine isosteres with bridgehead nitrogen. Part 1. Two independent syntheses of the [1, 2, 4] triazolo [1, 5-a][1, 3, 5] triazine ring system leading to a range of substituents in the 2, 5 and 7 positions | |
| Vainilavicius et al. | Synthesis of 5-(6-Methyl-2, 4-dioxo-1, 2, 3, 4-tetrahydro-3-pyrimidinyl)-methyl-4-amino-1, 2, 4-triazole-3-thione and its Reactions with Polyfunctional Electrophiles | |
| Aggarwal et al. | Visible-light-mediated regioselective synthesis of novel thiazolo [3, 2-b][1, 2, 4] triazoles: Advantageous synthetic application of aqueous conditions | |
| CS226940B1 (en) | 1,2-dihydrofuro (2,3 to 4,5) pyrolo (1,2-d)-1,2,4-triazi-1-ones and method of preparing same | |
| Mosselhi | A convenient synthesis of novelderivatives of pyrido [2, 3-d][1, 2, 4] triazolo [4, 3-a] pyrimidine-5, 6-dione | |
| Khan et al. | Condensed heterocycles: synthesis and antifungal activity of. pi.-deficient pyrimidines linked with. pi.-rich heterocycles | |
| Hajinasiri | Acetylenic esters in organic synthesis | |
| Hassan et al. | Chemistry and heterocyclization of carbohydrazides. | |
| Volovenko et al. | A Facile Route to the 6-Hetaryl Substituted Pyrrolo [1, 2-a] thieno [3, 2-e] pyrimidine Derivatives | |
| Farghaly et al. | Synthesis of imidazo [1, 2-c] pyrazolo [4, 3-e] pyrimidines derived from indole and related heterocycles | |
| NZ244983A (en) | Process for the preparation of process for the preparation of 5,7-diaryloxy-2-(heteroaryl)-1,2,4-triazolo[1,5-a][1,3,5]triazines | |
| Abdel-rahman et al. | Synthesis and antibacterial activities of some new thieno-[2, 3-b] quinolines | |
| Koreňová et al. | Synthesis and reactions of furocondensed systems containing indole skeleton | |
| Geies | A CONVENIENT SYNTHESIS OF DITHIENO [2, 3-b][2, 3-h] QUINOLINES AND PYRIMIDO [4′, 5′: 4, 5] THIENO [2, 3-b] THIENO [2, 3-h] QUINOLINES | |
| El-Taweel et al. | New and facile synthesis of substituted pyrrole, pyridine, pyrazolo [4, 3-b] pyridine, pyrano [3, 2-c] quinoline, napthopyran, naphthodipyran and coumarin derivatives | |
| Krutošíková et al. | Furan derivatives CXXVI. Synthesis and reactions of 3, 4-dichlorophenyl-substituted furocondensed derivatives | |
| CS228885B1 (en) | 1,4-dioxo-1,2,3,4-tetrahydrofuro/2,3 to 4,5/pyrolo/1,2-d/-1,2,4-triazines and method of preparing same | |
| Ahmed et al. | Fusion Reactions of N-Heterocyclic Moieties to Thiopyrano [4', 3': 4, 5] thieno [2, 3-d] pyrimidines | |
| Hassanien et al. | Synthesis of Some New Pyridines, Thienopyridines and Pyrido [2, 3: 4', 5'] thieno [3', 2'-d] pyrimidin-8-ones from 2 acetylbenzoimidazole | |
| Grytsak et al. | Synthesis of 6-chloro (dichloro-, trichloro-)-methyl-3-r-6, 7-dihydro-2h-[1, 2, 4] triazino [2, 3-c] quinazolin-2-ones and their modification in reactions with nucleophilic and non-nucleophilic bases | |
| Tumkevicius et al. | A simple synthesis of novel 6, 7, 8, 9-tetrahydro-2-thia-3, 5, 6, 9-tetraazabenz [cd] azulenes | |
| Haider et al. | Concise syntheses of 5-substituted pyridazino [4, 5-b] indolones and-diones |