Some Synthetic Applications of N‐Aminoheterocycles: Preparation of Bridgehead‐Nitrogen Heterocycles

Molina, P.

doi:10.1002/bscb.19860951104

Bulletin des Soc Chimique

1986

DOI: 10.1002/bscb.19860951104

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Some Synthetic Applications of N‐Aminoheterocycles: Preparation of Bridgehead‐Nitrogen Heterocycles

P. Molina

Abstract: P e d r o Molina Departamento d e Quimica O r g a n i c a , F a c u l t a d d e C i e n c i a s Quimicas y M a t e m a t i c a s , U n i v e r s i d a d d e Murcia, 30001 Murcia, S p a i n Some a s p e c t s of t h e c h e m i s t r y of t h e h e t e r o a r o m a t i c N-imines and t h e i r

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Cited by 10 publications

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Heterocyclization Reactions of Conjugated Heterocumulenes. Synthesis of Pyridine Derivatives by a Tandem Aza Wittig/Electrocyclization Strategy

et al. 1989

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The aza Wittig reaction of iminophosphorane 3 with isocyanates leads to conjugated carbodiimides 4, which undergo electrocyclic ring closure to give ethyl 2-pyridinecarboxylates 5. Iminophosphorane 9 reacts with nitromethane and acetone in a 1 : 1 molar ratio to form 10 and 11, respectively. Reaction of 9 with nitromethane in 1 : 3 molar ratio yields the iminophosphorane 12. The structure of 12 has been established by X-ray crystallography. Iminophosphoranes 10 and 11 react with isocyanates or carbon dioxide to give the pyrazolo [3,4b] It has become increasingly apparent that a$-unsaturated heterocumulenes are highly useful as synthetic intermediates in preparative heterocyclic chemistry. Especially cycloaddition reactions of such unsaturated heterocumulenic systems as, e. g., ketenes, isocyanates, isothiocyanates, and ketene imines provide an attractive plex of thermally induced 671 electrocyclizations of conjugated heterocumulenes have been documented 'I; only the thermal cyclization isocyanates6', 0-carbarnoylvinyl isocyanates 'I, and P-substituted vi-with heterocumulenes, e. g. carbon dioxide, carbon disulfide, and isocyanates or isothiocyanates, is a very useful reaction in synthetic heterocyclic chemistry'! Consequently, improvements which increase the efficiency or enlarge its applicability are always desirable, ing a moiety able to react with the aza Wittig product is important in this respect., Continuing our interest in the iminophosphorane-mediated synthesis of heterocycles, we describe a simple and apparently general procedure for the synthesis of conjugated heterocumulenes and the first synthesis of pyridine derivatives by electrocyclic ring closure of conjugated carbodiimides, isothiocyanates, and isocyanates. and ethyl azidoacetate or from azidoformylazoles and activated methylene compounds. R2$R4entry to a variety of heterocycles? However, relatively few exarn-

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Heterocyclization Reactions of Conjugated Heterocumulenes. Synthesis of Pyridine Derivatives by a Tandem Aza Wittig/Electrocyclization Strategy

et al. 1989

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ChemInform Abstract: Some Synthetic Applications of N‐Aminoheterocycles: Preparation of Bridgehead‐Nitrogen Heterocycles

Molina

1987

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Ring‐Opening Reactions of Mesoionic [1,2,4]Triazolo[1,5‐c]quinazolines. – Preparation of 1,2,4‐Triazolo[3,4‐b][1,3,4]thiadiazoles by a Translocative Rearrangement

et al. 1989

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1‐Amino‐5‐aryl‐2‐mercapto‐1H[1,2,4]triazolo[1,5‐c]quinazolin‐4‐ium hydroxides, inner salts (1) undergo ring opening by the action of hydrochloric acid to give 4‐amino‐3‐[2‐(aroylamino)‐phenyl]‐4,5‐dihydro‐5‐thioxo‐1H‐1,2,4‐triazoles 3. Reaction of compounds 3 with phosphorus pentasulfide yields the corresponding 1,2,4‐triazolo[3,4‐b][1,3,4]thiadiazoles 6. The molecular structure of 6b has been solved by X‐ray diffraction methods.

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Some Synthetic Applications of N‐Aminoheterocycles: Preparation of Bridgehead‐Nitrogen Heterocycles

Cited by 10 publications

References 7 publications

Heterocyclization Reactions of Conjugated Heterocumulenes. Synthesis of Pyridine Derivatives by a Tandem Aza Wittig/Electrocyclization Strategy

Heterocyclization Reactions of Conjugated Heterocumulenes. Synthesis of Pyridine Derivatives by a Tandem Aza Wittig/Electrocyclization Strategy

ChemInform Abstract: Some Synthetic Applications of N‐Aminoheterocycles: Preparation of Bridgehead‐Nitrogen Heterocycles

Ring‐Opening Reactions of Mesoionic [1,2,4]Triazolo[1,5‐c]quinazolines. – Preparation of 1,2,4‐Triazolo[3,4‐b][1,3,4]thiadiazoles by a Translocative Rearrangement

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