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Synthesis of functionalized nitrogen heterocycles by radical decarboxylation of beta- and gamma-amino acids

Iodinated or oxygenated nitrogen heterocycles are obtained by radical decarboxylation of beta- and gamma-amino acids. This mild, versatile reaction is applied to the synthesis of bioactive products, such as 4-arylpiperidines, hydroxylated piperidines, and new antifungal agents.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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Acid-Mediated Intermolecular [3 + 2] Cycloaddition toward Pyrrolo[2,1-a]isoquinolines: Total Synthesis of the Lamellarin Core and Lamellarin G Trimethyl Ether

A novel one-pot reaction has been developed for the efficient synthesis of pyrrolo[2,1-a]isoquinolines and 1-dearyllamellarin core from (E)-(2-nitrovinyl)benzenes and azomethine ylides generated in situ. This strategy provides a concise total synthesis of the lamellarin core and lamellarin G trimethyl ether using electrophilic substitution and palladium-catalyzed Suzuki-Miyaura cross-coupling reactions.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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MDR reversal agents

Compounds of the general formula: STR1 wherein R1, R2, R3, R4 and R5 are herein described, A is a straight or branched (C2 -C12)alkyl or a phenyl moiety and B is a moiety of the formula: STR2 The compounds are effective in potentiating the activity of chemotherapeutic anti-cancer agents by increasing the sensitivity of multi-drug resistant cells to such chemotherapeutic agents.

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Bronchorelaxing compounds

A compound of the general formula (I) including its pharmaceutically acceptable acid addition salts wherein A is CHR9, wherein R9 is H, C1-C6 alkyl; n is 1-3; B is CHR10, wherein R10 is H, C1-C6 alkyl; m is 1 or 2; D is O or S or optionally NR16, wherein R16 is H, C1-C6 alkyl or C2-C6 acyl; E is CR11R12 or NR13, wherein R11 and R12 are, independent of each other, H or C1-C6 alkyl, R13 is H or C1-C6 alkyl; F is C1-C18 alkyl which may be mono- or di-unsaturated and/or substituted, is useful in treating and preventing pulmonary disease characterized by bronchoconstriction. Also disclosed are pharmaceutical compositions comprising the compound and methods for their manufacture.

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Extracurricular laboratory:new discovery of 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline

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C-H functionalization of tertiary amines by cross dehydrogenative coupling reactions: Solvent-free synthesis of alpha-aminonitriles and beta-nitroamines under aerobic condition

A solvent-free synthesis of alpha-aminonitriles and beta-nitroamines by oxidative cross-dehydrogenative coupling under aerobic condition is reported. A catalytic amount of molybdenum(vi) acetylacetonoate was found to catalyze cyanation of tertiary amines to form alpha-aminonitriles, whereas vanadium pentoxide was found to promote aza-Henry reaction to furnish beta-nitroamines. Both of these environmentally benign reactions are performed in the absence of solvents using molecular oxygen as an oxidant.

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The singlet excited state of BODIPY promoted aerobic cross-dehydrogenative-coupling reactions under visible light

In contrast to previous studies, we disclose for the first time that the singlet excited state (1PS?) of BODIPY rather than the triplet excited state (3PS?) can drive C-H bond activation to form C-C and C-P bonds smoothly, which offers new methods to promote organic transformation under visible light irradiation.

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Benzytriphenylphosphonium borohydride (BTPPB) as a selective reducing agent for reduction of imines, enamines, and reductive amination of aldehydes with primary and secondry amines in methanol

Benzyltriphenyltriphenylphosphonium borohydride (BTPPB) (1) generated as white solid from benzyltriphenylphosphonium chloride and sodium borohydride is found to be a selective and versatile reducing agent. The reagent in methanol is very useful for reduction of imines, enamines and reductive animation of aldehydes.

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Reference£º
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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Receptor Antagonists

The present invention provides an alpha2c-adrenoceptor antagonist comprising, as an active ingredient, a condensed-ring-pyrimidine derivative represented by general formula (I) below or a pharmaceutically acceptable salt thereof useful for treating and/or preventing various diseases induced by hyperactivity of alpha2c-adrenoceptor (for example, Parkinson”s disease, L-DOPA-induced dyskinesia, tardive dyskinesia and depression) and the like. 1 {wherein p represents an integer of 1 to 3; R1 represents a substituted or unsubstituted heterocyclic group, substituted or unsubstituted aryl, or the like;R2 represents ?N(?R4)(?R5) (wherein R4 and R5 are the same or different, and each represents a hydrogen atom, substituted or unsubstituted aralkyl, or the like, or R4 and R5 form a substituted or unsubstituted heterocyclic group together with the adjacent nitrogen atom) or the like; and-Q- represents ?N?C(?R7)? [wherein R7 represents ?N(?R9)(?R10) (wherein R9 and R10 are the same or different, and each represents substituted or unsubstituted aralkyl, or the like, or R9 and R10 form a substituted or unsubstituted heterocyclic group together with the adjacent nitrogen atom) or the like] or the like}

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Reference£º
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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One-pot selective cleavage of prenyl carbamates using iodine in methanol followed by zinc

The prenyloxycarbonyl (Preoc) moiety was efficiently removed from carbamates to provde the corresponding amines in good to excellent yields (63-88 percent) by using iodine in methanol followed by treatment of the resulting beta-methoxyiodides by zinc powder. The reaction conditions are compatible with the presence of a number of functional groups such as Boc and Cbz carbamates, sulfides, double bonds, indoles and aromatic methyl ethers.

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Reference£º
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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alpha-Alkylation of tertiary amines by C(sp3)?C(sp3) cross-coupling under redox neutral photocatalysis

Direct alpha-alkylation of N-phenyl-tetrahydroisoquinoline with alkyl selenides of desired alkyl chain length and functionality is reported by photoredox catalysis. Construction of hexahydro pyrrolo- and pyrido-isoquinoline scaffolds along with indolines and tetrahydroquinolines is also described by intramolecular C(sp3)?C(sp3) cross-couplings.

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Reference£º
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem