AR074813A1 - PROCEDURE FOR THE PREPARATION OF PIPERAZINDIONA DERIVATIVES - Google Patents

PROCEDURE FOR THE PREPARATION OF PIPERAZINDIONA DERIVATIVES

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Publication number
AR074813A1
AR074813A1 ARP090104995A AR074813A1 AR 074813 A1 AR074813 A1 AR 074813A1 AR P090104995 A ARP090104995 A AR P090104995A AR 074813 A1 AR074813 A1 AR 074813A1
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AR
Argentina
Prior art keywords
alkyl
alkynyl
alkenyl
alkoxy
amino
Prior art date
Application number
Other languages
Spanish (es)
Original Assignee
Basf Se
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.)
Filing date
Publication date
Application filed by Basf Se filed Critical Basf Se
Publication of AR074813A1 publication Critical patent/AR074813A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
    • C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/18—Oxygen or sulfur atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Reivindicación 1: Procedimiento de preparación de derivados de piperazindiona de la fórmula (1), en donde R1 es alquilo C1-8, alcoxi C1-6-alquilo C1-6, alquenilo C3-6, alquinilo C3-6, CH2CN y alquil C1-8-carbonilo, en donde R1 puede estar parcial o totalmente sustituido con grupos Ra; R2 es alquilo C1-6, alquenilo C3-4 y alquinilo C3-4; A, B son, de modo independiente entre sí, arilo o heterociclilo monocíclico de 5 o 6 miembros o bicíclico de 9 o 10 miembros saturado, parcialmente insaturado o aromático, que contiene 1, 2, 3 o 4 heteroátomos seleccionados de O, N y S, que son grupos cíclicos unidos a través de alquileno C1-4 o alquilideno C1-4 y que pueden estar parcial o totalmente sustituidos con grupos Ra könen, Ra es halógeno, CN, NO2, alquilo C1-4, Z-cicloalquilo C3-6, haloalquilo C1-4, alcoxi C1-4, haloalcoxi C1-4, O-Z-cicloalquilo C3-6, S(O)nRy, alquenilo C2-6, Z-cicloalquenilo C3-6, alquenil C3-6-oxi, alquinilo C2-6, alquinil C3-6-oxi, NRARB, tri-alquil C1-4-sililo, Z-C(=O)-Ra1, Z-P(=O)(Ra1)2, fenilo, naftilo, heterociclo monocíclico de 3 a 7 miembros o bicíclico de 9 o 10 miembros saturado, insaturado o aromático unido a través de C o N, que contiene 1, 2, 3 o 4 heteroátomos seleccionados de O, N y S, que puede estar parcial o totalmente sustituido con grupos Raa y/o Ra1; Ry es alquilo C1-6, alquenilo C3-4, alquinilo C3-4, NRARB, y haloalquilo C1-4 y n representa 0, 1 o 2; RA, RB son, de modo independiente entre sí, hidrógeno, alquilo C1-6, alquenilo C3-6 y alquinilo C3-6; RA, RB también pueden formar junto con el átomo de nitrógeno al que están unidos un anillo saturado, parcial o totalmente insaturado de cinco o seis miembros, que, además de átomos de carbono, puede contener 1, 2 o 3 heteroátomos seleccionados de O, N y S, cuyo anillo puede estar sustituido con 1 a 3 grupos Raa; Z es un enlace covalente, aIquileno C1-4, alquenilo C2-6 o alquinilo C2-6; Ra1 es hidrógeno, OH, alquilo C1-8, haloalquilo C1-4, cicloalquilo C3-6, alquenilo C2-8, cicloalquenilo C5-6, alquinilo C2-8, alcoxi C1-6, haloalcoxi C1-4, alquenil C3-8-oxi, alquinil C3-8-oxi, NRARB, alcoxi C1-6-amino, alquil C1-6-sulfonilamino, alquil C1-6-aminosulfonilamino, [di-alquil C1-6)-amino]sulfonilamino, alquenil C3-6-amino, alquinil C3-6-amino, N-(alquenil C2-6)-N-(alquil C1-6)-amino, N-(alquinil C2-6)-N-(alquil C1-6)-amino, N-(alcoxi C1-6)-N-(alquil C1-6)-amino, N-(alquenil C2-6)-N-(alcoxi C1-6)-amino, N-(alquinil C2-6)-N-(alcoxi C1-6)-amino, alquil C1-6-sulfonilo, tri-alquil C1-4-sililo, fenilo, fenoxi, fenilamino y heterociclo monocíclico de 5 o 6 miembros o bicíclico de 9 o 10 miembros, que contiene 1, 2, 3 o 4 heteroátomos seleccionados de O, N y S, en donde los grupos cíclicos no están sustituidos o están sustituidos con 1, 2, 3, o 4 grupos Raa; Raa es halógeno, OH, CN, NO2, alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, haloalcoxi C1-4, S(O)nRy, Z-C(=O)-Ra1 y tri-alquil C1-4-sililo; y R3 es hidrógeno, halógeno, CN, NO2, OH, NH2, alquilo C1-4, Z-cicloalquilo C3-8, Z-cicloalquenilo C5-8, Z-cicloalquinilo C7-8, alquenilo C3-6, alquinilo C3-6, Z-[tri-alquil C1-6-sililo], Z-fenilo, heterociclo monocíclico de 5 o 6 miembros o bicíclico de 9 o 10 miembros saturado, parcialmente insaturado o aromático unido a través de Z, que contiene 1, 2, 3 o 4 heteroátomos seleccionados de O, N y S; caracterizado porque los derivados de piperazindiona de la fórmula (2), en la que al menos un grupo de R1 y R2 es hidrógeno y las otras variables presentan el significado según la fórmula 1, se hacen reaccionar con agentes de alquilación de la fórmula (3) R-X en donde X es grupo saliente nucleofílico y R es alquilo C1-8, alcoxi C1-6-alquilo C1-6, alquenilo C3-6, alquinilo C3-6 y CH2CN en condiciones básicas en un sistema bifásico en presencia de un catalizador de transferencia de fases.Claim 1: Preparation process for piperazindione derivatives of the formula (1), wherein R1 is C1-8 alkyl, C1-6 alkoxy-C1-6 alkyl, C3-6 alkenyl, C3-6 alkynyl, CH2CN and C1 alkyl -8-carbonyl, wherein R1 may be partially or totally substituted with Ra groups; R2 is C1-6 alkyl, C3-4 alkenyl and C3-4 alkynyl; A, B are, independently of each other, 5 or 6 membered monocyclic aryl or heterocyclyl or 9 or 10 saturated bicyclic, partially unsaturated or aromatic, containing 1, 2, 3 or 4 heteroatoms selected from O, N and S, which are cyclic groups linked through C1-4 alkylene or C1-4 alkylidene and which may be partially or totally substituted with Ra könen groups, Ra is halogen, CN, NO2, C1-4 alkyl, Z3 cycloalkyl- 6, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, OZ-C3-6 cycloalkyl, S (O) nRy, C2-6 alkenyl, C3-6 alkynyl, C3-6-oxy alkynyl, alkynyl C2-6, C3-6-oxy alkynyl, NRARB, tri-C1-4 alkyl-silyl, ZC (= O) -Ra1, ZP (= O) (Ra1) 2, phenyl, naphthyl, monocyclic heterocycle from 3 to 7 9 or 10 saturated or unsaturated or aromatic 9 or 10-membered bicyclic members linked through C or N, containing 1, 2, 3 or 4 heteroatoms selected from O, N and S, which may be partially or totally substituted with Raa and / or Ra1; Ry is C1-6 alkyl, C3-4 alkenyl, C3-4 alkynyl, NRARB, and C1-4 haloalkyl and n represents 0, 1 or 2; RA, RB are, independently of one another, hydrogen, C1-6 alkyl, C3-6 alkenyl and C3-6 alkynyl; RA, RB can also form together with the nitrogen atom to which a saturated, partially or totally unsaturated ring of five or six members is attached, which, in addition to carbon atoms, can contain 1, 2 or 3 heteroatoms selected from O, N and S, whose ring may be substituted with 1 to 3 Raa groups; Z is a covalent bond, C1-4 alkylene, C2-6 alkenyl or C2-6 alkynyl; Ra1 is hydrogen, OH, C1-8 alkyl, C1-4 haloalkyl, C3-6 cycloalkyl, C2-8 alkenyl, C5-6 cycloalkenyl, C2-8 alkynyl, C1-6 alkoxy, C1-4 haloalkoxy, C3-8 alkenyl -oxy, C3-8-oxy alkynyl, NRARB, C1-6-amino alkoxy, C1-6-sulfonylamino alkyl, C1-6-alkylsulfonylamino, [di- C1-6 alkyl) -amino] sulfonylamino, C3-6 alkenyl -amino, C3-6 alkynyl-amino, N- (C2-6 alkenyl) -N- (C1-6 alkyl) -amino, N- (C2-6 alkynyl) -N- (C1-6 alkyl) -amino, N- (C1-6 alkoxy) -N- (C1-6 alkyl) -amino, N- (C2-6 alkenyl) -N- (C1-6 alkoxy) -amino, N- (C2-6 alkynyl) -N - (C1-6 alkoxy) -amino, C1-6-sulfonyl alkyl, tri-C1-4 alkyl-silyl, phenyl, phenoxy, phenylamino and 5 or 6 membered monocyclic heterocycle or 9 or 10 membered bicyclic, containing 1 , 2, 3 or 4 heteroatoms selected from O, N and S, where the cyclic groups are not substituted or substituted with 1, 2, 3, or 4 Raa groups; Raa is halogen, OH, CN, NO2, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, S (O) nRy, ZC (= O) -Ra1 and tri-C1-4 alkyl -silyl; and R3 is hydrogen, halogen, CN, NO2, OH, NH2, C1-4 alkyl, Z3-8 cycloalkyl, C5-8 cycloalkenyl, C7-8 Z-cycloalkynyl, C3-6 alkenyl, C3-6 alkynyl , Z- [tri-C 1-6 alkyl-silyl], Z-phenyl, 5- or 6-membered monocyclic heterocycle or 9 or 10-saturated saturated, partially unsaturated or aromatic bicyclic linked through Z, containing 1, 2, 3 or 4 heteroatoms selected from O, N and S; characterized in that the piperazindione derivatives of the formula (2), in which at least one group of R1 and R2 is hydrogen and the other variables have the meaning according to the formula 1, are reacted with alkylating agents of the formula (3 ) RX where X is a nucleophilic leaving group and R is C1-8 alkyl, C1-6 alkoxy-C1-6 alkyl, C3-6 alkenyl, C3-6 alkynyl and CH2CN under basic conditions in a biphasic system in the presence of a catalyst of phase transfer.

ARP090104995 2008-12-19 2009-12-18 PROCEDURE FOR THE PREPARATION OF PIPERAZINDIONA DERIVATIVES AR074813A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP08172397 2008-12-19

Publications (1)

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AR074813A1 true AR074813A1 (en) 2011-02-16

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Family Applications (1)

Application Number Title Priority Date Filing Date
ARP090104995 AR074813A1 (en) 2008-12-19 2009-12-18 PROCEDURE FOR THE PREPARATION OF PIPERAZINDIONA DERIVATIVES

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AR (1) AR074813A1 (en)
WO (1) WO2010069819A1 (en)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AR058408A1 (en) * 2006-01-02 2008-01-30 Basf Ag PIPERAZINE COMPOUNDS WITH HERBICITY ACTION
US20090137396A1 (en) * 2006-01-05 2009-05-28 Basf Se Piperazine Compounds with a Herbicidal Action
TW200906805A (en) * 2007-06-12 2009-02-16 Basf Se Piperazine compounds having herbicidal action

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Publication number Publication date
WO2010069819A1 (en) 2010-06-24

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