The steric hindrance controlled [2]pseudorotaxanes constructed by V-type stilbene dyes⊂CB[7]

In this paper, five V-type stilbene dyes (VD, 1a-1e) that had unchanged dimethylamino phenylethenyl (DMPE) arm as inclusive location with CB[7] and another arm with different steric hindrance aryloxyethyl (AE) group were designed and synthesized. Their inclusive characteristics and stability to CB[7] were studied. Fluorescence spectroscopy and ¹H NMR method were used respectively to study the inclusive characteristics of 1a?CB[7], 1b?CB[7], 1c?CB [7], 1d?CB[7] and 1e?CB[7]. Fitting curves results of fluorescent titration indicated that 1:1 complexes between CB[7] and VD were constructed, and their inclusive constants were calculated respectively. The order of inclusive constants K_1a?CB[7]> K_1b?CB[7]> K_1c?CB[7] > K_1d?CB[7] was consistent with the magnitude of the steric hindrance, however, 1e did not include with CB[7]. Therefore, a series of steric hindrance controlled [2]pseudorotaxanes were constructed.     

CHEMICAL BEHAVIOR OF SOME BENZ[b] INDENO[1,2-e] [1,4] THIAZINE DERIVATIVES

Abstract

The study of the chemical behavior of some benz[b] indeno[1,2-e] [1,4] thiazine derivatives was accomplished. Different reactivities were observed for 4b,5-dihydrobenz[b]-indeno[1,2-e] [1,4] thiazine-10α(11H)-ol (3) and 5-ethyl-4b,5-dihydrobenz[b] indeno[1,2-e]-[1,4] thiazine-10α(11H)-ol (5); 3 is reoxidated to benz[b] indeno[1,2-e] [1,4] thiazine-10α(11H)-ol (2), while 5 undergoes transposition and oxidation to spiro[3-ethylbenzo-thiazol-2(3H), 1′-indan-2′-one] (6). Possible pathways for these transformations are discussed.     

1,3-Disubstitutedpyrazole-4-caboxaldehyde in Heterocyclic Synthesis: A Novel Synthesis of Pyridine-2(1H)-thione and Fused Nitrogen and/or Sulfur Heterocyclic Derivatives

Pyridine-2(1H)-thione 5 was synthesized from the reaction of 3-[3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl]-1-phenylpropenone (3) and cynothioacetamide (4). Compound 5 reacted with halogented compounds 6a–e to give 2-S-alkylpyridine derivatives 7a–e, which could be in turn cyclized into the corresponding thieno[2,3-b]-pyridine derivatives 8a–e. Compound 8a reacted with hydrazine hydrate to give 9. The latter compound reacted with acetic anhydride (10a), formic acid (10b), acetic acid, ethyl acetoacetate, and pentane-2,4-dione to give the corresponding pyrido[3′,2′:4,5]thieno-[3,2-d]pyrimidine 13a,b, pyrazolo[3′,4′:4,5]thieno[3,2-d]pyridine 14 and thieno[2,3-b]-pyridine derivatives 18 and 20, respectively. Alternatively, 8c reacted with 10a,b and nitrous acid to afford the corresponding pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine 24a,b and pyrido[3′,2′:4,5]thieno[3,2-d][1,2,3]triazine 26 derivatives, respectively. Finally compound 5 reacted with methyl iodide to give 2-methylthiopyridine derivative 27, which could be reacted with hydrazine hydrate to yield the corresponding pyrazolo[3,4-b]-pyridine derivative 29.     

Hockey-stick liquid crystalline 6-oxoverdazyl§

A series of hockey-stick shaped 6-oxoverdazyl radicals 1[n]–3[n], containing CH₃ (a), CF₃ (b) and CN (c) groups in the short ‘arm’, were prepared and their physical properties were investigated. Mesogenic behaviour was found only in the CN derivatives with the COO (1[n]c) and N=N (2[12]c) linking groups, which exhibited a nematic phase. Analysis of binary mixtures of selected compounds with bent-core nematic host 4[12] gave virtual nematic-isotropic transition temperatures, [T_NI], which follow the order 1[12]b < 1[12]c < 1[12]a in one series and 1[12]c < 2[12]c < (3[12]c) in another. The observed effectiveness of the short-arm substituent, CF₃ < CN < CH₃, was related to the magnitude and orientation of the molecular dipole moment calculated with density functional theory methods.     

Utility of 1‐Chloro‐3,4‐dihydronaphthalene‐2‐carboxaldehyde in the Synthesis of Novel Heterocycles with Pharmaceutical Interest

Ethyl α‐cyano‐β‐(1‐chloro‐3,4‐dihydronaphthalene‐2‐yl) acrylate (2) was prepared by the Knoevenagel condensation of 1 with ethyl cyanoacetate. Compound 2 was used as the key intermediate to prepare Schiff bases (3a, b), benzo[c]acridine (4), naphthyl thiopyrimidine (5), and pyrazolo[2,3‐a]‐benzo[h]quinazoline (6) derivatives through its reaction with hydrazines, p‐ansidine, thiourea, and 3,5‐diamino‐4‐phenylazopyrazole, respectively. Base‐catalyzed cyclocondensation of 1 with hippuric acid gives oxazolone derivative (7). Reaction of compound 7 with aniline gave imidazolone derivative (9). Treatment of compound 1 with different types of diaminopyrazoles gave 6,7‐dihydro‐pyrazolo[2,3‐a]‐benzo[h]quinazoline (10–13) derivatives. The multicomponent reaction of compound 1 with pyrazolone and malononitrile in the presence of ammonium acetate furnished pyrazolo[3,4‐b]‐benzo[h]quinoline (14) while in the presence of piperidine afforded benzo[h]chromeno[2,3‐c]pyrazole derivative 15.     

Ein Beitrag zur Chemie des 2,3-Dihydro-3-oxo-benzo[b]thiophen-1,1-dioxids Synthesen mit Nitrilen, 86. Mitt.

Summary 2,3-Dihydro-3-oxo-benzo[b]thiophen-1,1-dioxide (1) reacts as CH-acidic component with amidines of orthoesters and anilines resp. to give the anilinomethylene derivates3, 4, and5. With triethyl orthoformiate the hydroxymethylene-compound7 is obtained. Anilino- and phenylhydrazino derivates8 and9 prove the carbonyl activity of1, azo-coupling leads to10, whereas treatment of1 with sulfur and malononitrile yields the benzo[b]thieno[2,3-d]thiophenes11. Introduction of substituents with active NH-functions in position 2 of the dicyanomethylene-product2, such as azocoupling, reaction with phenyl isocyanate and formation of enamines, leads to ring closure reactions between a nitrile and the NH-group. Thereby the phenyl-benzo[4,5]thieno[2,3-c]pyridazines12, the phenyl-1H-benzo[4,5]thieno[2,3-c]pyridines13 and the phenylamino-benzo[4,5]thieno[2,3-c]pyridines14 are obtained.¹³C and¹⁵N-NMR spectroscopy was used as proof of the ring closure reactions.

     

Metal ion-assisted assembly of one-dimensional polyrotaxanes incorporating cucurbit[6]uril

Three cucurbit[6]uril (CB[6])-based polyrotaxanes [Cu(H₂ C6N4)(CB[6])]Cl₄·12H₂O (1), [Co(H₂ C6N4)(CB[6])]Cl₄·14H₂O (2) and [Ag(C6N4)(CB[6])]NO₃·7H₂O (3) are prepared using N,N′-bis(4-pyridylmethyl)-1,6-hexanediamine (C6N4) threading into CB[6]'s and metal ions' assistance. Single-crystal X-ray diffraction analyses reveal that polyrotaxanes 1, 2 and 3 all have 1D chain structure where 1 and 2 are linear and 3 has two shapes, linear and sawtooth, respectively. The effects of guest molecules, metal and counter ions as well as intermolecular weak interactions on the architectures of polyrotaxanes are discussed.     

Synthesis of some fused quinoline derivatives

Summary Preparations of the novel fused dimethoxyquinoline derivatives of furo[2,3-b]quinoline (5),s-triazolo[4,3-a]quinoline (8) and tetrazolo[1,5-a]quinoline (10) from 6,7-dimethoxy-3-car-boxyquinoline-1-oxide (1) are reported.

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Synthese kondensierter Chinolinderivate

Zusammenfassung Die Synthese der neuen kondensierten Dimethoxy-Chinolinderivate Furo[2,3-b]chinolin (5),s-Triazolo[4,3-a]chinolin (8) und Tetrazolo[1,5-a]chinolin (10) aus 6,7-Dimethoxy-3-carboxychinolin-1-oxid (1) wird beschrieben.

     

Conformational effects on mesophase stability: numerical comparison of carborane diester homologous series with their bicyclo[2.2.2]octane,cyclohexane and benzene analogues

Three series of diesters of 4‐alkoxyphenols containing 12‐vertex p‐carborane (1A[n], n = 1–22), 10‐vertex p‐carborane (1B[n], n = 1–12) or bicyclo[2.2.2]octane (1C[n], n = 1–12) as the central structural element were prepared and investigated by optical and calorimetric methods. All carborane diesters exhibited exclusively nematic behaviour, whereas the carbocyclic analogues 1C[n] and also cyclohexane (1D[n]) and benzene (1E[n]) derivatives, showed early onset of SmA phase and complete disappearance of nematic behaviour. The isotropic transition temperatures, T _MI, for the five series of mesogens were analysed numerically using a three‐parameter exponential function. The resulting limiting values, T _MI(∞), provided a quantitative assessment of the central element ability to support the mesogenic state. They demonstrated that, whereas the T _MI(∞) values for the carbocycles, C, D, and E, are around 125°C, for carboranes A and B this value is 70±2°C and 49±19°C, respectively. Two types of comparative analysis of trends in T _MI relative to those of the terephthalate series 1E[n] demonstrated abnormal behaviour of both carborane series (1A[n] and 1B[n]) and also the cyclohexane series (1D[n]). The former showed progressive destabilisation of the mesophase, whereas the series 1D[n] exhibited increasing mesophase stability relative to 1E[n] with increasing chain length. Both of these effects were explained using conformational analysis of theoretical models and experimental molecular structures for 1A[3], 1B[4] and 1C[4]. The increasing relative destabilisation of the mesophase in the carborane derivatives was rationalised by the high order rotational axes in A and B and D _4d symmetry for B. The trend of the ΔT _MI values for series 1D[n] was explained with the existence of the equatorial‐axial conformational equilibrium for the cyclohexane derivatives. The clearing temperatures for the hypothetical pure diequatorial conformers 1D[n]‐ee were estimated.     

2-[3-(Trifluoromethyl)phenyl]furo[3,2-b]pyrroles: synthesis and reactions

The synthesis and reactions of methyl 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole-5-carboxylate (1a) are described. Upon reaction with methyl iodide, benzyl chloride, or acetic anhydride, this compound gave N-substituted products 1b-d. By hydrolysis of compounds 1a-c, the corresponding acids 2a-c were formed, or by reaction with hydrazine-hydrate, the corresponding carbohydrazides 3a-c were formed. By heating 2-[3-(trifluoromethyl)phenly]-4H-furo[3,2-b]pyrrole-5-carboxylic acid (2a) in acetic anhydride, 4-acetyl-2-[3-(trifluoromethyl)phenyl]furo[3,2-b]pyrrole (4) was formed. By hydrolysis of 4, 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole (5a) was formed, and reactions with methyl iodide or benzyl chloride gave N-substituted products 5b-c. The reaction of 4 with dimethyl butynedioate gave substituted benzo[b]furan 6. Compound 3a reacted with triethyl orthoesters giving 7a-c, which afforded with phosphorus (V) sulphide the corresponding thiones 8a-c. The thiones 8a-c reacted with hydrazine hydrate to form hydrazine derivatives 9a-c. The reaction of triethyl orthoformiate with compounds 9a-c led to furo[2′,3′: 4,5]pyrrolo[1,2-d][1,2,4]triazolo[3,4-f][1,2,4]triazines 10a-c. Hydrazones 11a-c were formed from 3a-c and 5-[3-(trifluoromethyl)phenyl]furan-2-carboxaldehyde. The effect of microwave irradiation on some condensation reactions was compared with “classical” conditions. The results showed that microwave irradiation shortens the reaction time while affording comparable yields.     

BENZOQUINOLINES II. SYNTHESIS OF SOME NEW BENZO[h] PYRIMIDO [4′,5′:4,5]THIENO[2,3-b]QUINOLINE DERIVATIVES AND RELATED FUSED HEXACYCLIC SYSTEMS

Abstract

Reaction of 8-amino-7-(2 furyl)-5,6-dihydrobenzo[h]thieno[2,3-b]quinoline-9-carbonitrile (3a) with phenyl isothiocyanate, triethyl orthoformate, ethylenediamine and/or sodium azide afforded benzo[h]thieno[2,3-b]quinolines 4,7,20 and 25 respectively. Cyclization of thiourea derivative 4 furnished thioxopyrimidine derivative 5. The dithioxopyrimidine 6 was prepared by reaction of 3a with carbon disulfide. On treatment of 7 with hydrazine hydrate, 10-amino-7-(2-furyl)-11-imino-5,6,10,11-tetrahydrobenzo[h]pyrimido[4′,5′:4,5]thieno [2,3-b]quinoline (8) was obtained. Compounds 8,20 and 25 were used as key intermediates in the synthesis of the fused hexacyclic compounds 9–19, 21–24 and 26–28 respectively. 8-Amino-7-(2-furyl)-5,6-dihydrobenzo[h]thieno[2,3-b]quinoline-9-carboxamide (3b) was reacted with some reagents, namely triethyl orthoformate, benzaldehyde, carbon disulfide, phenyl isothiocyanate, and/or acetic anhydride to give the corresponding benzo[h]pyrimido [4′,5′: 4,5]thieno[2,3-b]quinolines 29, 30, 31, 32 and 34. Compound 29 underwent some sequence reactions to give 37–42. Some of the prepared compounds were tested in vitro for their antibacterial and antifungal activities.     

SYNTHESIS AND NMR CHARACTERIZATION OF P-VINYL SUBSTITUTED PHOSPHAZENE PRECURSORS1

Abstract

The reactions of either PhPCl₂ or PCl₃ with (Me₃Si)₂NLi followed by H₂C[dbnd]CHMgBr were used to prepare the new P-vinyl substituted [bis(trimethylsilyl)amino]phosphines, (Me₃Si)₂NP(R)CH[dbnd]CH₂ [1: R=Ph, 2: CH[dbnd]CH₂, 3: R=Me, and 4: R=N(SiMe₃)₂]. Oxidative bromination of phosphines 3–1 afforded the P-bromo-P-vinyl-N-(trimethylsilyl)phosphoranimines, Me₃SiN[dbnd]P(CH[dbnd]CH₂)(R)Br [5: R=Ph, 6: R=CH[dbnd]CH₂, 7: R=Me], which, upon treatment with CF₃CH₂OH/Et₃N, were subsequently converted to the P-trifluoroethoxy derivatives, Me₃SiN[dbnd]P(CH[dbnd]CH₂)(R)OCH₂CF₃ [8: R=Ph, 9: R=CH[dbnd]CH₂, 10: R=Me]. Compounds 1–10, which are of interest as potential precursors to P-vinyl substituted poly(phosphazenes), were fully characterized by elemental analyses (except for the thermally unstable P-Br derivatives 5–7) and NMR spectroscopy (¹H, ¹³C, and ³¹P) including complete analysis of the vinylic proton splitting patterns via HOM2DJ experiments.     

SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF SOME NEW PYRIDYL DIARYLSULFIDE AND DIARYLSULFONES

Abstract

Condensation of isonicotinaldehyde with 4-aminodiphenyl sulfides 1 and/or sulfones II gave 4-[N-[p-(diaryl/thio)]formimidoyl]-pyridine III and/or 4-[N-[p-(diarylsulfonyl)]-formimidoyl]pyridine IV. Cyclocondensation of mercaptoacetic acid on III and IV gave 3-[p-(diarylthio)]-2-(4-pyridyl)-4-thiazolidinones V and 3-[p-(diarylsulfonyl)]-2-(4-pyridyl)-4-thiazolidinones VI respectively. (Hetero/arylthio)-N-(6-methyl-2-pyridyl)-acetamides VIII have been synthesised via interaction of 6-methyl-2-chloroacetamido-pyridine VII with heterocyclic and/or aromatic mercaptans. Reaction of VII with piperidine and/or morpholine affords (IX). Biological activities of these compounds were tested.     

Synthesis of Polyfunctionally Substituted Pyrazolonaphthyridine,Pentaazanaphthalene, and Heptaazaphenanthrene Derivatives

6-aminopyrazolo[3,4-b]pyridine-5-carbonitrile (2) was used as a precursor for the synthesis of a variety of pyrazolo[3,4-b][1,8]naphthyridines (3, 4) and pentaazacyclopenta[b]naphthalenes (5–10, 13, 14) via the initial addition to either the cyano or amino group followed by cyclization. Also, a series of heptaazadicyclopenta[a,g]naphthalenes (15–17) and heptaazacyclopenta[b]phenanthrenes (18, 19) were obtained via the interaction of 4-(dibenzothiophen-2-yl)-1,5-dihydro-5-imino-3-methyl-1-phenyl-1,2,6,8,9-pentaazacyclopenta[b]naphthalen-6-ylamine (14) with different reagents. The structures of the synthesized compounds were established by elemental and spectral analyses.     

Synthesis,structure, and in vitro cytotoxicity of organoplatinum(II) complexes containing aryl olefins and quinolines

Ten new organoplatinum(II) complexes, [PtCl(Saf)(8-OQ)] (1), [Pt(Saf-1H)(8-OQ)] (2), [PtCl(Meug)(8-OQ)] (3), [Pt(Meug-1H)(8-OQ)] (4), [PtCl(Meteug)(8-OQ)] (5), [PtCl(Meteug)(Q)] (6), [Pt(Meteug)(Q-COO)] (7), [Pt(Eteug-1H)(Q)] (8), [Pt(Eteug-1H)(8-OQ)] (9), and [Pt(Eteug-1H)(Q-COO)] (10) (where Saf = safrole, Meug = methyleugenol, Meteug = methyl eugenoxyacetate, Eteug = ethyl eugenoxyacetate, Q = quinoline, 8-OQ = 8-hydroxyquinolinate, and Q-COO = quinolin-2-carboxylate), were synthesized and characterized by spectroscopic methods. The position of N and O donors of quinoline ligands in comparison with the ethylenic double bond and the aromatic C5 of the aryl olefins in platinum(II) coordination sphere of 1–10 was determined using their NOESY spectra and confirmed by single-crystal X-ray diffraction of 10. Complexes 1, 2, 3, 4, and 9 exhibit impressive activities on four human cancer cell lines KB, Hep-G2, Lu, and MCF7 with IC₅₀ = 1.4–9.6 μM. Complexes 1, 2, 4, and 9 gave better antitumor activity than cisplatin against examined cell lines.     

Synthesis of pyrazolo[3,4-c]isoquinoline and pyrazolo[3,4-b]pyridine derivatives from azomethines and CH-acidic compounds

Summary Donor substituted arylidene aminopyrazoles1a–c and CH-acidic 1,3-dicarbonyl compounds2a–e give in ethanol in an addition/cyclization reaction pyrazolo[3,4-c]isoquinolines4a–i and pyrazolo[3,4-b]pyridine derivatives5a,b, respectively. Using ethyl cyanoacetate as CH-acidic component, cinnamate6 and the cyano substituted pyrazolo[3,4-b]pyridine7 are formed.

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Synthese von Pyrazolo[3,4-c]isochinolin- und Pyrazolo[3,4-b]pyridin-Derivaten aus Azomethinen und CH-aciden Verbindungen

Zusammenfassung Die Reaktion der donorsubstituierten Aryliden-aminopyrazole1a–c mit den CH-aciden 1,3-Dicarbonylverbindungen2a–e führt in einer Additions/Cyclisierungsreaktion zu den Pyrazolo[3,4-c]isochinolin-4a–i bzw. Pyrazolo[3,4-b]pyridin-Derivaten5a,b. Verwendet man Cyanessigester als CH-acide Komponente, werden der Zimtsäureester6 und das cyanosubstituierte Pyrazolo[3,4-b]pyridin7 gebildet.

     

A Convenient Synthesis of Novel Functionalized Pyrimido[5′,4′:4,5]thieno[3,2-c]pyridazines and Related Fused Systems

Possible approaches to the synthesis of functionalized, pyrimido[5′,4′:4,5]thieno [3,2-c]pyridazines 2-18 , pyridazino[3′,4′:4,5]thieno[2,3-d]triazines 19, 20a,b and pyrido[3′,2′:4,5]thieno[3,2-c]pyridazines 22a,b are described. The sequence involves the heterocyclization of 6-amino-1,3-diphenyl-1,4-dihydrothieno[3,2-c]pyridazine-7-carboxamide (1) with appropriate reagents. The antimicrobial activity of some the newly synthesized compounds was examined. All tested compounds proved to be active as antibacterial and antifungal agents.     

On the chemistry of pyridazines,XXXVI: Novel diaza-analogs of 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one

Procedures for the preparation of the novel tricyclic ketones 10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2—d]pyridazin-5-one (3), 5,6-dihydro-11H-benzo[4,5]cyclohepta[2,1—c]pyridazin-11-one (4), and 10,11-dihydro-5H-benzo[4,5]-cyclohepta[1,2—c]pyridazin-5-one (5) starting from a preformed 1,2-diazine system are proposed. The key intermediates7,19, and11 are prepared from (2-phenylethyl)pyridazines6 and18 by introduction of a carboxylic functionality via homolytic alkoxycarbonylation or via a sulfonylReissert-type reaction.

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Zur Chemie von Pyridazinen, 36. Mitt.: Neuartige Diazaanaloga des 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ons

Zusammenfassung Methoden zur Darstellung der neuen trizyklischen Ketone 10,11-Dihydro-5H-benzo[4,5]cyclohepta[1,2—d]pyridazine-5-on (3), 5,6-Dihydro-11H-benzo[4,5]cyclohepta[2,1—c]pyridazin-11-on (4) und 10,11-Dihydro-5H-benzo[4,5]cyclohepta[1,2—c]pyridazin-5-on (5) ausgehend von einem präformierten 1,2-Diazinsystem werden vorgeschlagen. Die Schlüsselbausteine dieser Synthesen7,19 und11 werden durch Einführung einer Carboxylfunktion in die (2-Phenylethyl)pyridazine6 und18 über homolytische Alkoxycarbonylierung bzw. eine Sulfonyl-Reissert-Reaktion erhalten.

     

Heterocycles With a Benzothiadiazepine Moiety. IV. Synthesis of Novel Tetracyclic Rings by Intramolecular Cyclization of 10-Bromoacetyl-10,11-dihydro-11-ethoxycarbonyl-pyrrolo[1,2-b] [1,2,5] Benzothiadiazepine 5,5-Dioxide and Its Derivatives

Two novel tetracyclic derivatives, namely 5 and 8, have been synthesized by intramolecular cyclization of the 10-bromoacetyl-10,11-dihydro-11-ethoxycarbonylpyrrolo[1,2-b] [1,2,5]benzothiadiazepine 5,5-dioxide (3) and, respectively, the bis-methylamide of 11-carboxy-10,11-dihydropyrrolo[1,2-b] [1,2,5]benzothiadiazepine-11-acetic acid 5,5-dioxide (4). The last compound formed when treating with an excess of methylamine either the lactam 5 or the diethyl ester of 11-carboxy-10,11-dihydropyrrolo[1,2-b] [1,2,5]benzothiadiazepine-11-acetic acid 5,5-dioxide (7). An unambiguous synthesis of the diester 7 was achieved to confirm the chemical structure of derivatives 4 and 5.     

Reaction of metal carbonyls with 2-hydroxy-1-naphthaldeyde methanesulfonylhydrazone and characterization of the substitution products

Five new complexes, [M(CO)₅(nafmsh)] [M?=?Cr, 1; Mo, 2; W, 3], [Re(CO)₄Br(nafmsh)], 4 and [Mn(CO)₃(nafmsh)], 5 have been synthesized by the photochemical reaction of metal carbonyls [M(CO)₆] (M?=?Cr, Mo, W), [Re(CO)₅Br], and [Mn(CO)₃Cp] with 2-hydroxy-1-naphthaldehyde methanesulfonylhydrazone (nafmsh). The complexes have been characterized by elemental analysis, EI mass spectrometry, FT-IR, and ¹H NMR spectroscopy. The spectroscopic studies show nafmsh is a monodentate ligand coordinating via the imine N donor atom in 1–4 and as a tridentate ligand in 5.