NO782087L - Fremgangsmaate ved fremstilling av kinazolinonoxyder - Google Patents

Fremgangsmaate ved fremstilling av kinazolinonoxyder

Info

Publication number: NO782087L
Authority: NO; Norway
Prior art keywords: formula; chloro; quinazolinone; mol; phenyl
Prior art date: 1977-06-16

Application number

NO782087A

Other languages

English (en)

Norwegian (no)

Inventor

William Joseph Middleton

Original Assignee

Du Pont

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-06-16

Filing date

1978-06-15

Publication date

1978-12-19

1978-06-15 Application filed by Du Pont filed Critical Du Pont

1978-12-19 Publication of NO782087L publication Critical patent/NO782087L/no

Links

238000000034 method Methods 0.000 title claims description 15
238000002360 preparation method Methods 0.000 title claims 4
150000001875 compounds Chemical class 0.000 claims description 13
239000012948 isocyanate Substances 0.000 claims description 11
150000002513 isocyanates Chemical class 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 7
239000007795 chemical reaction product Substances 0.000 claims description 7
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 4
125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 55
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 24
239000013078 crystal Substances 0.000 description 18
239000007787 solid Substances 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 13
PFNXVIDDDAFQRQ-UHFFFAOYSA-N C12=CC(Cl)=CC=C2NC(=O)[N+]([O-])=C1C1=CC=CC=C1 Chemical compound C12=CC(Cl)=CC=C2NC(=O)[N+]([O-])=C1C1=CC=CC=C1 PFNXVIDDDAFQRQ-UHFFFAOYSA-N 0.000 description 9
238000004519 manufacturing process Methods 0.000 description 8
239000012258 stirred mixture Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
FTAHQVWNRWZINV-UHFFFAOYSA-N 1-hydroxyquinazolin-2-one Chemical class C1=CC=C2C=NC(=O)N(O)C2=C1 FTAHQVWNRWZINV-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
239000000843 powder Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
ZUWXHHBROGLWNH-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-phenylmethanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 ZUWXHHBROGLWNH-UHFFFAOYSA-N 0.000 description 3
PZOZHMBWLDUJCP-UHFFFAOYSA-N 3-fluoro-1H-1,2-benzodiazepine Chemical class FC1=NNC2=C(C=C1)C=CC=C2 PZOZHMBWLDUJCP-UHFFFAOYSA-N 0.000 description 3
KVBZGDNWBRCXHF-UHFFFAOYSA-N 3-oxidoquinazolin-3-ium Chemical compound C1=CC=CC2=C[N+]([O-])=CN=C21 KVBZGDNWBRCXHF-UHFFFAOYSA-N 0.000 description 3
PIKZXHWPRIJZJN-UHFFFAOYSA-N 6-chloro-1-methyl-3-oxido-4-phenylquinazolin-3-ium-2-one Chemical compound [O-][N+]=1C(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 PIKZXHWPRIJZJN-UHFFFAOYSA-N 0.000 description 3
LOVPZNFLGAXZGT-UHFFFAOYSA-N 6-chloro-4-ethoxy-3,4-diphenyl-1h-quinazolin-2-one Chemical compound O=C1NC2=CC=C(Cl)C=C2C(OCC)(C=2C=CC=CC=2)N1C1=CC=CC=C1 LOVPZNFLGAXZGT-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 3
MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 2
DYPCOCOEFYSJHP-UHFFFAOYSA-N 1-(2-benzoyl-4-chlorophenyl)-1-methyl-3-phenylurea Chemical compound C=1C=C(Cl)C=C(C(=O)C=2C=CC=CC=2)C=1N(C)C(=O)NC1=CC=CC=C1 DYPCOCOEFYSJHP-UHFFFAOYSA-N 0.000 description 2
OKYIKPYUCUWSDO-UHFFFAOYSA-N 1-(2-benzoyl-4-chlorophenyl)-3-phenylurea Chemical compound C=1C=CC=CC=1C(=O)C1=CC(Cl)=CC=C1NC(=O)NC1=CC=CC=C1 OKYIKPYUCUWSDO-UHFFFAOYSA-N 0.000 description 2
CCEBWDWBJVBYFJ-UHFFFAOYSA-N 1-(2-benzoyl-4-chlorophenyl)-3-propan-2-ylurea Chemical compound CC(C)NC(=O)NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 CCEBWDWBJVBYFJ-UHFFFAOYSA-N 0.000 description 2
AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical compound C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
QIDCJFIPAIPVRT-UHFFFAOYSA-N 6-bromo-4-hydroxy-3-methyl-4-phenyl-1h-quinazolin-2-one Chemical compound CN1C(=O)NC2=CC=C(Br)C=C2C1(O)C1=CC=CC=C1 QIDCJFIPAIPVRT-UHFFFAOYSA-N 0.000 description 2
AWSGAAUIGPHERF-UHFFFAOYSA-N 6-chloro-4-hydroxy-3-methyl-4-phenyl-1h-quinazolin-2-one Chemical compound CN1C(=O)NC2=CC=C(Cl)C=C2C1(O)C1=CC=CC=C1 AWSGAAUIGPHERF-UHFFFAOYSA-N 0.000 description 2
DBKIXSRJBMRMMF-UHFFFAOYSA-N 6-chloro-4-phenyl-1h-quinazolin-2-one Chemical compound C12=CC(Cl)=CC=C2NC(=O)N=C1C1=CC=CC=C1 DBKIXSRJBMRMMF-UHFFFAOYSA-N 0.000 description 2
-1 6-substituted-4-phenylquinazolinone 3-oxides Chemical class 0.000 description 2
ZXBWHSQNFXUCLP-UHFFFAOYSA-N C1=CC=C2NC(=O)[N+]([O-])=CC2=C1 Chemical compound C1=CC=C2NC(=O)[N+]([O-])=CC2=C1 ZXBWHSQNFXUCLP-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
WPNMLCMTDCANOZ-UHFFFAOYSA-N [5-chloro-2-(methylamino)phenyl]-phenylmethanone Chemical compound CNC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 WPNMLCMTDCANOZ-UHFFFAOYSA-N 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
238000009835 boiling Methods 0.000 description 2
WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 2
150000002443 hydroxylamines Chemical class 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
239000003158 myorelaxant agent Substances 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
239000000932 sedative agent Substances 0.000 description 2
150000003672 ureas Chemical class 0.000 description 2
LXJVUGANBDAASB-UHFFFAOYSA-N (2-amino-5-bromophenyl)-phenylmethanone Chemical compound NC1=CC=C(Br)C=C1C(=O)C1=CC=CC=C1 LXJVUGANBDAASB-UHFFFAOYSA-N 0.000 description 1
DWFDQVMFSLLMPE-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanone Chemical compound FC1=CC=CC=C1C(=O)C1=CC=CC=C1 DWFDQVMFSLLMPE-UHFFFAOYSA-N 0.000 description 1
XHPPBGZNBZMKNH-UHFFFAOYSA-N 1,2-dihydro-1,2-benzodiazepin-3-one Chemical compound C1=CC(O)=NNC2=CC=CC=C21 XHPPBGZNBZMKNH-UHFFFAOYSA-N 0.000 description 1
ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 1
SDQJTWBNWQABLE-UHFFFAOYSA-N 1h-quinazoline-2,4-dione Chemical class C1=CC=C2C(=O)NC(=O)NC2=C1 SDQJTWBNWQABLE-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 1
ZNBNBTIDJSKEAM-UHFFFAOYSA-N 4-[7-hydroxy-2-[5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2-methyl-3-propanoyloxypentanoic acid Chemical compound C1C(O)C(C)C(C(C)C(OC(=O)CC)C(C)C(O)=O)OC11OC(C)(C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CC1 ZNBNBTIDJSKEAM-UHFFFAOYSA-N 0.000 description 1
JSTXCWJWQKRPIU-UHFFFAOYSA-N 6-chloro-1-methyl-4-phenylquinazolin-2-one Chemical compound N=1C(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 JSTXCWJWQKRPIU-UHFFFAOYSA-N 0.000 description 1
WQKHERPPDYPMNX-UHFFFAOYSA-N 6-chloro-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(Cl)=CC=C21 WQKHERPPDYPMNX-UHFFFAOYSA-N 0.000 description 1
YKTGQUPZGACWEI-UHFFFAOYSA-N 6-chloro-3-ethyl-4-(2-fluorophenyl)-4-hydroxy-1h-quinazolin-2-one Chemical compound CCN1C(=O)NC2=CC=C(Cl)C=C2C1(O)C1=CC=CC=C1F YKTGQUPZGACWEI-UHFFFAOYSA-N 0.000 description 1
BYLRNYNRGXIPPV-UHFFFAOYSA-N 6-chloro-3-ethyl-4-hydroxy-4-phenyl-1h-quinazolin-2-one Chemical compound CCN1C(=O)NC2=CC=C(Cl)C=C2C1(O)C1=CC=CC=C1 BYLRNYNRGXIPPV-UHFFFAOYSA-N 0.000 description 1
HKOOFQWBQATOSD-UHFFFAOYSA-N 6-chloro-4-(2-fluorophenyl)-1h-quinazolin-2-one Chemical compound FC1=CC=CC=C1C1=NC(=O)NC2=CC=C(Cl)C=C12 HKOOFQWBQATOSD-UHFFFAOYSA-N 0.000 description 1
PUOYDTRFCAVAPT-UHFFFAOYSA-N 6-chloro-4-hydroxy-1,3-dimethyl-4-phenylquinazolin-2-one Chemical compound C12=CC(Cl)=CC=C2N(C)C(=O)N(C)C1(O)C1=CC=CC=C1 PUOYDTRFCAVAPT-UHFFFAOYSA-N 0.000 description 1
241000208202 Linaceae Species 0.000 description 1
235000004431 Linum usitatissimum Nutrition 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
BNFUPOXNFMFOLD-UHFFFAOYSA-N N=C=O.NC1=CC=CC=C1C(=O)C1=CC=CC=C1 Chemical compound N=C=O.NC1=CC=CC=C1C(=O)C1=CC=CC=C1 BNFUPOXNFMFOLD-UHFFFAOYSA-N 0.000 description 1
AGKPGIOZNCJFTQ-UHFFFAOYSA-N [2-(methylamino)phenyl]-phenylmethanone Chemical compound CNC1=CC=CC=C1C(=O)C1=CC=CC=C1 AGKPGIOZNCJFTQ-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
QBRSFUSGKXVSPM-UHFFFAOYSA-N hydroxylamine;hydrobromide Chemical compound Br.ON QBRSFUSGKXVSPM-UHFFFAOYSA-N 0.000 description 1
229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 1
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
229960004592 isopropanol Drugs 0.000 description 1
229940035363 muscle relaxants Drugs 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/80—Oxygen atoms
- C07D239/82—Oxygen atoms with an aryl radical attached in position 4

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pretreatment Of Seeds And Plants (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

NO782087A 1977-06-16 1978-06-15 Fremgangsmaate ved fremstilling av kinazolinonoxyder NO782087L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US80707677A	1977-06-16	1977-06-16

Publications (1)

Publication Number	Publication Date
NO782087L true NO782087L (no)	1978-12-19

Family

ID=25195510

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO782087A NO782087L (no)	1977-06-16	1978-06-15	Fremgangsmaate ved fremstilling av kinazolinonoxyder

Country Status (16)

Country	Link
EP (1)	EP0000149A1 (da)
JP (1)	JPS545988A (da)
AT (1)	ATA436678A (da)
AU (1)	AU3709278A (da)
CA (1)	CA1094068A (da)
DK (1)	DK176378A (da)
ES (1)	ES470828A1 (da)
FI (1)	FI781928A7 (da)
GR (1)	GR64944B (da)
IT (1)	IT1098341B (da)
NO (1)	NO782087L (da)
NZ (1)	NZ187581A (da)
PL (1)	PL113420B1 (da)
PT (1)	PT68174A (da)
SU (1)	SU797575A3 (da)
ZA (1)	ZA783438B (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP3553062A1 (en)	2018-04-09	2019-10-16	Chemical Intelligence Limited	Antimicrobial and anticancer cationic phthalocyanine compounds

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS4946633B2 (da) *	1971-08-17	1974-12-11

1978
- 1978-04-24 DK DK176378A patent/DK176378A/da unknown
- 1978-06-14 CA CA305,471A patent/CA1094068A/en not_active Expired
- 1978-06-14 AU AU37092/78A patent/AU3709278A/en active Pending
- 1978-06-15 IT IT24615/78A patent/IT1098341B/it active
- 1978-06-15 EP EP78100163A patent/EP0000149A1/en not_active Withdrawn
- 1978-06-15 PT PT68174A patent/PT68174A/pt unknown
- 1978-06-15 NO NO782087A patent/NO782087L/no unknown
- 1978-06-15 ZA ZA00783438A patent/ZA783438B/xx unknown
- 1978-06-15 NZ NZ187581A patent/NZ187581A/xx unknown
- 1978-06-15 ES ES470828A patent/ES470828A1/es not_active Expired
- 1978-06-15 AT AT436678A patent/ATA436678A/de not_active Application Discontinuation
- 1978-06-15 SU SU782627504A patent/SU797575A3/ru active
- 1978-06-16 JP JP7367978A patent/JPS545988A/ja active Pending
- 1978-06-16 FI FI781928A patent/FI781928A7/fi not_active Application Discontinuation
- 1978-06-16 GR GR56539A patent/GR64944B/el unknown
- 1978-06-16 PL PL1978207682A patent/PL113420B1/pl not_active IP Right Cessation

Also Published As

Publication number	Publication date
ATA436678A (de)	1981-01-15
CA1094068A (en)	1981-01-20
SU797575A3 (ru)	1981-01-15
PT68174A (en)	1978-07-01
GR64944B (en)	1980-06-10
AU3709278A (en)	1979-12-20
FI781928A7 (fi)	1978-12-17
ES470828A1 (es)	1979-10-01
EP0000149A1 (en)	1979-01-10
IT1098341B (it)	1985-09-07
PL207682A1 (pl)	1979-05-07
IT7824615A0 (it)	1978-06-15
JPS545988A (en)	1979-01-17
NZ187581A (en)	1980-11-28
PL113420B1 (en)	1980-12-31
DK176378A (da)	1978-12-17
ZA783438B (en)	1979-06-27

Publication	Publication Date	Title
CA1102330A (en)	1981-06-02	Process for preparing alkylenediamine derivatives
CA2130924A1 (en)	1993-09-30	Preparation of substituted guanidines
ISHIKAWA et al.	1980	Cyclic guanidines. IX. Synthesis of 2-amino-3, 4-dihydroquinazolines as blood platelet aggregation inhibitors
Shi et al.	2020	Fluorinated alcohol mediated N, N′-dialkylation of amino acid derivatives via cascade [1, 5]-hydride transfer/cyclization for concise synthesis of tetrahydroquinazoline
NZ203954A (en)	1986-01-24	N,n'-disubstituted polymethylene diamines
US4258187A (en)	1981-03-24	Process for preparing quinazolinone oxides
NO782087L (no)	1978-12-19	Fremgangsmaate ved fremstilling av kinazolinonoxyder
US4183932A (en)	1980-01-15	Fused quinazolinones and preparation thereof
US4183930A (en)	1980-01-15	Amino derivatives of pyrazolo [1,5-a]s-triazine, and their therapeutic applications
US4228167A (en)	1980-10-14	Diuretic and vasodilating tricyclic quinazolines
DE3784795T2 (de)	1993-06-24	Verfahren zur herstellung von 5,6-substituierten-2,4-chinazolindiaminen und zwischenprodukten.
Dunn et al.	1986	New reactions of deoxyvasicinone. Part 4
US4268511A (en)	1981-05-19	3-Amino(1H,3H)quinazoline-2,4-dione derivatives and their therapeutic applications
US3272816A (en)	1966-09-13	7-amino-2, 4-dioxo-1, 2, 3, 4-tetrahydropyrido[2, 3-d]pyrimidines
Puodziunaite et al.	2000	On the synthetic way to novel peri-annelated imidazo [1, 5] benzodiazepinones as the potent non-nucleoside reverse transcriptase inhibitors
Rodriguez et al.	1968	Synthesis of 4, 5-dihydro-3H-1, 3-benzodiazepines and 4, 5-dihydro-1H-2, 4-benzodiazepines
NAGAHARA et al.	1976	Reaction of ο-Aminobenzamide Derivatives with Ethoxymethylenemalononitrile and Its Analogue
CA1219264A (en)	1987-03-17	Benzobisoxazinetetrones
US3738985A (en)	1973-06-12	Certain 3-(3-amino-2-benzoyloxypropyl)-4(3h)-quinazolinones
Love et al.	1968	Reaction of 2-phenyl-1-pyrroline with phenyl isocyanate
US3985732A (en)	1976-10-12	1,2,3,11A-Tetrahydro-10-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5,11(10H)-diones
Downes et al.	1950	Application of the amidomethylation reaction to the synthesis of quinazolines
US3629262A (en)	1971-12-21	Process for preparing 4-phenyl-quinazolines
PL97091B1 (pl)	1978-02-28	Sposob wytwarzania nowych podstawionych n-/2-pirolidynyloalkilo/benzamidow
US3968230A (en)	1976-07-06	Compositions containing benzodiazepindiones and method of use