NO771296L - Reduksjonsprosess. - Google Patents

Reduksjonsprosess.

Info

Publication number: NO771296L
Authority: NO; Norway
Prior art keywords: methyl; hydrogen; indole; borohydride; alkyl
Prior art date: 1976-04-15

Application number

NO771296A

Other languages

English (en)

Norwegian (no)

Inventor

Joel Gilbert Berger

Original Assignee

Endo Lab

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.)

1976-04-15

Filing date

1977-04-14

Publication date

1977-10-18

1977-04-14 Application filed by Endo Lab filed Critical Endo Lab

1977-10-18 Publication of NO771296L publication Critical patent/NO771296L/no

Links

238000011946 reduction process Methods 0.000 title 1
-1 amino-substituted indoles Chemical class 0.000 claims description 48
239000001257 hydrogen Substances 0.000 claims description 39
229910052739 hydrogen Inorganic materials 0.000 claims description 39
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 32
238000000034 method Methods 0.000 claims description 31
150000001875 compounds Chemical class 0.000 claims description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 19
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
150000002431 hydrogen Chemical class 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 16
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 14
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 13
150000002367 halogens Chemical group 0.000 claims description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
239000000460 chlorine Chemical group 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 9
239000011541 reaction mixture Substances 0.000 claims description 9
125000001309 chloro group Chemical group Cl* 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
230000000707 stereoselective effect Effects 0.000 claims description 7
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
229910000033 sodium borohydride Inorganic materials 0.000 claims description 6
239000012279 sodium borohydride Substances 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
239000011593 sulfur Substances 0.000 claims description 6
125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 5
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
239000000047 product Substances 0.000 description 12
UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 12
239000000725 suspension Substances 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
229910000085 borane Inorganic materials 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
239000000243 solution Substances 0.000 description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
230000001624 sedative effect Effects 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
150000002475 indoles Chemical class 0.000 description 4
239000003921 oil Substances 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000011343 solid material Substances 0.000 description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000932 sedative agent Substances 0.000 description 3
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000000561 anti-psychotic effect Effects 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
YKRAMTOSINBJFJ-PIMYIBFHSA-N (4ar,9br)-2-(1-adamantylmethyl)-5-phenyl-3,4,4a,9b-tetrahydro-1h-pyrido[4,3-b]indole Chemical compound C1([C@H]2[C@H]3CCN(C2)CC24CC5CC(CC(C5)C2)C4)=CC=CC=C1N3C1=CC=CC=C1 YKRAMTOSINBJFJ-PIMYIBFHSA-N 0.000 description 1
NOPNHYOMKNZREG-JTHBVZDNSA-N (4ar,9br)-2-(cyclopentylmethyl)-5-phenyl-3,4,4a,9b-tetrahydro-1h-pyrido[4,3-b]indole Chemical compound C([C@@H]1[C@H](N(C2=CC=CC=C21)C=1C=CC=CC=1)CC1)N1CC1CCCC1 NOPNHYOMKNZREG-JTHBVZDNSA-N 0.000 description 1
CJWPRFAPIUPOSX-DOTOQJQBSA-N (4ar,9br)-5-phenyl-1,2,3,4,4a,9b-hexahydropyrido[4,3-b]indole Chemical compound C1([C@H]2[C@H]3CCNC2)=CC=CC=C1N3C1=CC=CC=C1 CJWPRFAPIUPOSX-DOTOQJQBSA-N 0.000 description 1
MXQGFCYOYZUVDR-FUHWJXTLSA-N (4ar,9br)-8-bromo-5-(4-bromophenyl)-2-methyl-3,4,4a,9b-tetrahydro-1h-pyrido[4,3-b]indole Chemical compound C1([C@H]2[C@H]3CCN(C2)C)=CC(Br)=CC=C1N3C1=CC=C(Br)C=C1 MXQGFCYOYZUVDR-FUHWJXTLSA-N 0.000 description 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical class C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 1
239000012448 Lithium borohydride Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
TVJORGWKNPGCDW-UHFFFAOYSA-N aminoboron Chemical compound N[B] TVJORGWKNPGCDW-UHFFFAOYSA-N 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
239000002249 anxiolytic agent Substances 0.000 description 1
230000000949 anxiolytic effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910010277 boron hydride Inorganic materials 0.000 description 1
UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
230000006378 damage Effects 0.000 description 1
ZJULYDCRWUEPTK-UHFFFAOYSA-N dichloromethyl Chemical compound Cl[CH]Cl ZJULYDCRWUEPTK-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
230000006742 locomotor activity Effects 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000003672 processing method Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000007790 scraping Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Indole Compounds (AREA)
Superconductors And Manufacturing Methods Therefor (AREA)
Saccharide Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO771296A 1976-04-15 1977-04-14 Reduksjonsprosess. NO771296L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US67743876A	1976-04-15	1976-04-15

Publications (1)

Publication Number	Publication Date
NO771296L true NO771296L (no)	1977-10-18

Family

ID=24718701

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO771296A NO771296L (no)	1976-04-15	1977-04-14	Reduksjonsprosess.

Country Status (17)

Country	Link
US (1)	US4217454A (de)
JP (1)	JPS52128371A (de)
AR (1)	AR215135A1 (de)
AT (1)	AT353784B (de)
CA (1)	CA1107279A (de)
DD (1)	DD129980A5 (de)
DK (1)	DK165877A (de)
ES (1)	ES457822A1 (de)
FI (1)	FI771185A7 (de)
GR (1)	GR63654B (de)
LU (1)	LU77139A1 (de)
MX (1)	MX4737E (de)
NL (1)	NL7703900A (de)
NO (1)	NO771296L (de)
PT (1)	PT66441B (de)
SE (1)	SE7702300L (de)
SU (1)	SU831072A3 (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5328905A (en) *	1987-07-20	1994-07-12	Duphar International Research B.V.	8,9-anellated-1,2,3,4-tetrahydro-β-carboline derivatives
DK686688A (da) *	1987-12-14	1989-06-15	Duphar Int Res	8,9-annelerede beta-carboliner, deres fremstilling og laegemidler indeholdende forbindelserne
JP2009505079A (ja) *	2005-08-12	2009-02-05	セレリティ・インコーポレイテッド	気泡検出を用いた流れの測定および制御

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3932650A (en) *	1973-01-22	1976-01-13	E. I. Du Pont De Nemours & Company	Trans-octahydropyridoindolobenzazepines as central nervous system depressants
US3890327A (en) *	1973-05-11	1975-06-17	Du Pont	Trans-1,2,3,4,4a,8,9,14a-octahydropyrido(r',3':2,3)indolo(1,7-ab)+8 1)benzazepine
AR205452A1 (es) *	1973-12-06	1976-05-07	Endo Lab	Metodo para preparar nuevos trans-2, 3, 4, 4a, 5, 9b-hexahidro-5-fenil-1h-pirido(4,3-b) indoles
CA1026331A (en) *	1973-12-06	1978-02-14	Joel G. Berger	Substituted indolobenzazepines
GB1464431A (en) *	1974-03-25	1977-02-16	Roche Products Ltd	Indolobenzazepine derivatives and a process for the manufacture thereof
US4091102A (en) *	1975-08-22	1978-05-23	Endo Laboratories, Inc.	Anti-depressant trans-hexahydropyrido[3,4-b]indoles
SE7702301L (sv) *	1976-04-08	1977-10-09	Endo Lab	Trans-hexahydro-pyrido-indoler

1977
- 1977-03-02 SE SE7702300A patent/SE7702300L/xx not_active Application Discontinuation
- 1977-04-07 NL NL7703900A patent/NL7703900A/xx not_active Application Discontinuation
- 1977-04-13 SU SU772468607A patent/SU831072A3/ru active
- 1977-04-13 CA CA276,124A patent/CA1107279A/en not_active Expired
- 1977-04-14 FI FI771185A patent/FI771185A7/fi not_active Application Discontinuation
- 1977-04-14 PT PT66441A patent/PT66441B/pt unknown
- 1977-04-14 NO NO771296A patent/NO771296L/no unknown
- 1977-04-14 ES ES457822A patent/ES457822A1/es not_active Expired
- 1977-04-14 AT AT262277A patent/AT353784B/de not_active IP Right Cessation
- 1977-04-14 DK DK165877A patent/DK165877A/da unknown
- 1977-04-15 JP JP4272277A patent/JPS52128371A/ja active Pending
- 1977-04-15 GR GR53218A patent/GR63654B/el unknown
- 1977-04-15 LU LU77139A patent/LU77139A1/xx unknown
- 1977-04-15 MX MX775643A patent/MX4737E/es unknown
- 1977-04-15 DD DD7700198425A patent/DD129980A5/de unknown
- 1977-04-15 AR AR267244A patent/AR215135A1/es active
1978
- 1978-07-26 US US05/928,191 patent/US4217454A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
DD129980A5 (de)	1978-02-22
US4217454A (en)	1980-08-12
JPS52128371A (en)	1977-10-27
SE7702300L (sv)	1977-10-16
FI771185A7 (de)	1977-10-16
PT66441B (pt)	1978-09-22
ATA262277A (de)	1979-05-15
MX4737E (es)	1982-08-25
LU77139A1 (de)	1977-11-14
ES457822A1 (es)	1978-08-01
GR63654B (en)	1979-11-28
DK165877A (da)	1977-10-16
CA1107279A (en)	1981-08-18
NL7703900A (nl)	1977-10-18
SU831072A3 (ru)	1981-05-15
PT66441A (pt)	1977-05-01
AT353784B (de)	1979-12-10
AR215135A1 (es)	1979-09-14

Publication	Publication Date	Title
Lizos et al.	2003	Concise synthesis of (±)-horsfiline and (±)-coerulescine by tandem cyclisation of iodoaryl alkenyl azides
Schoemaker et al.	1980	Stereocontrolled synthesis of functionalized 1-azaspirans: Efficient synthesis of perhydrohistrionicotoxin
NO760401L (de)	1976-08-17
AU600582B2 (en)	1990-08-16	A process for the preparation of substituted indolin-2-one derivatives
NO771296L (no)	1977-10-18	Reduksjonsprosess.
NO750341L (de)	1975-09-01
Bailey et al.	1997	New asymmetric route to bridged indole alkaloids: formal enantiospecific syntheses of (-)-suaveoline,(-)-raumacline and (-)-N b-methylraumacline
NO790704L (no)	1979-09-11	Lukkeinnretning for ifyllingsstasjonen ved ekstrudere
Rubiralta et al.	1988	Synthesis and reactivity of 2-(1', 3'dithian-2'-yl) indoles
Mangelinckx et al.	2010	Diastereoselective synthesis of 6-functionalized 4-aryl-1, 3-oxazinan-2-ones and their application in the synthesis of 3-aryl-1, 3-aminoalcohols and 6-arylpiperidine-2, 4-diones
Gassman et al.	1965	The synthesis of 2-azabicyclo [2.2. 1] heptanes by the Hofmann-Löffler-Freytag reaction
Matier et al.	1971	Novel cyclizations and ring-opening reactions of 3-phenylindene derivatives
Liu et al.	2003	Stereoselective synthesis of 2-amino-2-deoxysugars: N-alkyl-D-allosamines
TWI423957B (zh)	2014-01-21	吡啶硼烷複合物
Smith et al.	1993	Synthetic approaches to homotropanes and homotrop-7-enes using intramolecular displacement and amidomercuration strategies
Dell'Erba et al.	1975	The behaviour of 2‐nitrothiophene and of 3‐nitrothiophene with some nucleophiles
Brimble et al.	2005	Efficient synthesis of the azabicyclo [3.3. 1] nonane ring system in the alkaloid methyllycaconitine using bis (alkoxymethyl) alkylamines as aminoalkylating agents in a double Mannich reaction
Luo et al.	2023	NBS-induced intramolecular annulation reactions for the divergent synthesis of fused-and spirocyclic indolines
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